Pyridine carboxamide derivatives and their use as pesticides

ABSTRACT

The invention relates to 3-pyridylcarboxamide derivatives of the formula (I):  
                 
wherein the various symbols are as defined in the description, compositions thereof, methods for controlling pests by applying same, and processes for their preparation.

The invention relates to 3-pyridylcarboxamide derivatives and their use for the control of pests, in particular arthropods such as insects and acarids, and helminths (including nematodes); to compositions containing them, and to processes and intermediates for their preparation.

The control of insects, nematodes or helminths with 3-pyridylcarboxamide compounds has been described in many patents such as EP 580374, JP 10101648, JP 10182625, WO 200109104, WO 200114340, JP 6321903, JP 10195072 and JP 11180957.

However, the level of action and/or duration of action of these prior-art compounds is not entirely satisfactory in all fields of application, in particular against certain organisms or when low concentrations are applied.

Since modern pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, use spectrum, toxicity, combination with other active substances, combination with formulation auxiliaries or synthesis, and since the occurrence of resistances is possible, the development of such substances can never be regarded as concluded, and there is constantly a high demand for novel compounds which are advantageous over the known compounds, at least as far as some aspects are concerned.

It is an object of the present invention to provide compounds which widen the spectrum of the pesticides in various aspects.

The present invention provides a compound which is a 3-pyridylcarboxamide derivative of formula (I):

wherein: R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a); R² is H, (C₁-C₆)alkyl or R³; R³ is R⁵, OH or NH₂; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);

R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more (C₁-C₆)alkyl, (C₁-C₆)haloalkyl or R⁶ groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups are substituted by one or more R⁶ groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or substituted by one or more R⁶ groups; R⁴ is H or R⁵; or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups (preferred examples of such ring systems include pyrrolidin-1-yl, pyrrolin-1-yl, piperidin-1-yl, morpholin-1-yl (or its N-oxide), thiomorpholin-1-yl (or its S-oxide or S,S-dioxide), 4,5-dihydropyrazol-1-yl or pyrazol-1-yl); R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, CO(C₁-C₆)alkyl, NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl or SO₂(C₁-C₆)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is NH(CHR¹⁴)_(s)aryl, —(CR¹⁵R¹⁶)_(p)aryl, O(R¹⁵R¹⁶)_(r)aryl, NHCOaryl, CO(CH₂)_(t)aryl, NHSO₂aryl, SO₂(CH₂)_(u)aryl or N═C(aryl)₂, —(CR¹⁵R¹⁶)_(p)heterocyclyl or O(R¹⁵R¹⁶)_(r)heterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; or is O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl or N═C[(C₁-C₆)alkyl]₂; R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, CO₂(C₁-C₆)alkyl, CO₂H, NO₂, OH, amino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, carbamoyl, (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl or CH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by one or more R^(14a) or halogen groups; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S, O or NR¹⁸; V is O or S; W is (CHR¹⁹)_(q), CO or NR²⁰; X is CR²¹ or N; Y is CR²² or N; Z is O, CO or NR²³; R⁷, R⁸, R⁹, R¹², R¹⁹, R²¹ and R²² are each independently H; or (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy or (C₂-C₆)alkynyloxy, which last seven mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl, which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom may represent C═O; R¹⁰, R²⁰ and R²³ are each independently H; or (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or (C₃-C₈)cycloalkyl, which last four mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; R¹¹ is R⁷, halogen, CN, CO₂(C₁-C₆)alkyl, NO₂ or S(O)_(n)R¹⁴; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; R¹³ is R⁷ or OH; R¹⁴, R¹⁵ and R¹⁶ are each independently H, (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R¹⁸ is R⁷ or OH; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; m is zero or one; n, p, r, s, t and u are each independently zero, one or two; q is one, two or three; and each heterocyclyl in the above mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1 to 4 hetero atoms selected from N, O and S; or a pesticidally acceptable salt thereof; with the exclusion of the compound wherein R¹ is —C(═U)NR³R⁴; U is O; R² is H; m is zero; R⁴ is H and R³ is 2,4-dichlorophenyl.

These compounds possess valuable pesticidal properties.

The invention also encompasses any stereoisomer, enantiomer or geometric isomer, and mixtures thereof.

By the term “pesticidally acceptable salts” is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for pesticidal use. Suitable salts with bases, e.g. formed by compounds of formula (I) containing a carboxy or OH group, include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.

The term pests means arthropod pests (including insects and acarids), and helminths (including nematodes).

In the present patent specification, including the accompanying claims, the aforementioned substituents have the following meanings:

halogen atom means fluorine, chlorine, bromine or iodine;

alkyl groups and portions thereof (unless otherwise defined) may be straight- or branched-chain;

cycloalkyl groups preferably have from three to six carbon atoms in the ring and are optionally substituted by halogen or alkyl.

The haloalkyl and haloalkoxy groups can bear one or more halogen atoms; preferred groups of this type include —CF₃ and —OCF₃.

The term “halo” before the name of a radical means that this radical is partially or completely halogenated, that is to say, substituted by F, Cl, Br, or I, in any combination, preferably by F or Cl.

The expression “(C₁-C₆)-alkyl” is to be understood as meaning an unbranched or branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms, such as, for example a methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical.

“(C₁-C₆)-Haloalkyl” is to be understood as meaning an alkyl group mentioned under the expression “(C₁-C₆)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl or the 1,1,2,2-tetrafluoroethyl group.

“(C₁-C₆)-Alkoxy” is to be understood as meaning an alkoxy group whose hydrocarbon radical has the meaning given under the expression “(C₁-C₆)-alkyl”.

The terms “alkenyl” and “alkynyl” with a range of carbon atoms stated as prefix denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms which corresponds to this stated range and which contains at least one multiple bond which can be located in any position of the respective unsaturated radical. “(C₂-C₆)-Alkenyl” accordingly denotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or the hexenyl group. “(C₂-C₆)-Alkynyl” denotes, for example, the ethynyl, propargyl, 2-methyl-2-propynyl; 2-butynyl; 2-pentynyl or the 2-hexynyl group.

“(C₃-C₈)-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, and denotes bicyclic alkyl radicals, such as the norbornyl radical.

The expression “(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl” is to be understood as meaning, for example the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl, 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl or the 4-tert-butylcyclohexyl radical.

“(C₁-C₆)-Alkylamino” denotes a nitrogen atom which is substituted by an alkyl radical of the above definition. “Di-(C₁-C₆)-alkylamino” denotes a nitrogen atom which is substituted by two alkyl radical of the above definition.

The expression “(C₁-C₆)-alkylcarbamoyl” denotes a carbamoyl group having one hydrocarbon radical which has the meaning given under the expression “(C₁-C₆)-alkyl”; and “di-(C₁-C₆)-alkylcarbamoyl” denotes a carbamoyl group having two hydrocarbon radicals which can be identical or different.

The expression “aryl” is to be understood as meaning a carbocyclic, i.e. constructed of carbon atoms, aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl.

The expression “heterocyclyl” preferably denotes a cyclic radical which can be completely saturated, partially unsaturated or completely unsaturated and which contains in the ring one or more identical or different atoms selected from the group consisting of nitrogen, sulfur and oxygen, where, however, two oxygen atoms may not be directly adjacent and at least one carbon atom has to be present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine, piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine, thiazolidine, oxirane or oxetane radical.

Heterocyclyl preferably denotes a saturated, partially saturated or aromatic ring system having 3 to 7 ring members and 1 to 4 heteroatoms selected from the group consisting of O, S and N, where at least one carbon atom has to be present in the ring.

More preferably, heterocyclyl denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,3,4)-thiadiazole, (1,2,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrimidine, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine or thiazolidine radical (particularly a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,3,4)-thiadiazole, 1,2,4-thiadiazole, thiazole, pyrazole, pyrrole, isoxazole, benzothiazole, 1,2,4-triazole, pyrazine, pyridazine, oxirane or oxetane radical).

Preferred substituents for the various aliphatic, aromatic and heterocyclic ring systems include halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, phenyl, benzyl or phenoxy, where in the alkyl radicals and the radicals derived therefrom one or more—and in the case of fluorine up to the maximum number of—hydrogen atoms can be replaced by halogen, preferably chlorine or fluorine.

More preferred substituents include halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio.

Most preferred substituents include halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio.

It is to be generally understood, unless otherwise stated, that the term “unsubstituted or substituted by one or more groups” or “unsubstituted or substituted by one or more groups selected from” means that such groups (or preferred groups) may be the same or different.

R¹ is preferably —C(═U)NR³R⁴;

R² is preferably H or R³ (more preferably R² is H);

R³ is preferably R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups;

or preferably R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):

R⁴ is preferably H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups (particularly preferred examples of such ring systems include pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl or its S-oxide or S,S-dioxide); R⁵ is preferably (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or is —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl, O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; (more preferably R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or is —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl, O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups); R⁶ is preferably halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, NO₂ or OH; (more preferably R⁶ is halogen or CN); R¹⁷ is preferably R⁶, R^(14a) or CH₂OH; U is preferably S or O; W is preferably (CHR¹⁹)_(q) or CO; Z is preferably 0; R⁷, R⁸, R⁹, R¹⁰ and R¹⁹ are each preferably H; or (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom represent C═O; R¹⁴, R¹⁵ and R¹⁶ are each preferably H or (C₁-C₆)alkyl; R^(14a) is preferably (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; m is preferably zero; n, r, s, t and u are preferably zero or one; q is preferably one; and heterocyclyl preferably denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,2,4)-thiadiazole, (1,3,4)-thiadiazole, benzothiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrimidine, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane radical.

A preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a);

R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more (C₁-C₆)alkyl, (C₁-C₆)haloalkyl or R⁶ groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups are substituted by one or more R^(6a) groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or substituted by one or more R⁶ groups;

R^(6a) is (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CO₂(C₁-C₆)alkyl, CO₂H, amino, (C₀-C₆)alkylamino, carbamoyl, (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl or CH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by one or more R^(14a) or halogen groups;

and the other values are as defined in formula (I).

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

R² is H;

R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups;

or R² and R³ together with the interconnecting atoms may form a heterocyclic ring selected from (A) and (C):

R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl or thiomorpholin-1-yl (or its S-oxide or S,S-dioxide) ring; R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl, O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, NO₂ or OH; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S or O; W is (CHR¹⁹)_(q) or CO; Z is O; R⁷, R⁸, R⁹, R¹⁰ and R¹⁹ are each H; or (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom represent C═O; R¹⁴, R¹⁵ and R¹⁶ are each H or (C₁-C₆)alkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; m is zero; n, r, s, t and u are zero, one or two; q is one; and wherein heterocyclyl denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,2,4)-thiadiazole, (1,3,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane radical.

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

R² is H;

U is O or S;

R³ is (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl(C₁-C₆)alkyl, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, NH₂, (C₁-C₆)alkylamino, OH, Ophenyl, pyrimidyl, benzothiazolyl, thiazolyl, thiadiazolyl, —(CH₂)₂pyrrolidin-1-yl, NHSO₂phenyl, NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl, NHCOphenyl or N═C(phenyl)₂; or is pyridyl unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN and NO₂; or is OCH₂phenyl which phenyl is unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl, CN and NO₂; or is (C₁-C₆)alkoxy unsubstituted or substituted by a CO₂(C₁-C₆)alkyl group;

or is —(CHR¹⁵)_(p)phenyl wherein p is 0, 1 or 2, R¹⁵ is H or (C₁-C₆)alkyl, and phenyl is unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, CN, NO₂, OH, CH₂OH, CO₂(C₁-C₆)alkyl and phenoxy which phenoxy is unsubstituted or substituted by one or more groups selected from halogen and (C₁-C₆)haloalkyl;

or is (C₁-C₆)alkyl unsubstituted or substituted by one or more groups selected from (C₁-C₆)alkoxy, CN, OH, CO₂(C₁-C₆)alkyl and CH[O(C₁-C₆)alkyl]₂;

or is NH(CH₂)_(s)phenyl wherein s is zero or 1;

R⁴ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, —(CH₂)_(p)phenyl wherein p is 0 or 1, or N═C[(C₁-C₆)alkyl]₂;

or R³ and R⁴ together with the adjacent N atom may form a pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl which groups are unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl and OH; or form a 4,5-dihydropyrazol-1-yl ring; and

m is zero.

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

-   U is O; -   R² is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl; or     is (C₁-C₆)alkyl substituted by CO₂(C₁-C₆)alkyl or CH[O(C₁-C₆)alky]₂;     R³ is (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, CH₂phenyl or OCH₂phenyl;     or is (C₁-C₆)alkoxy unsubstituted or substituted by one or two     CO₂(C₁-C₆)alkyl groups;     R⁴ is H or (C₁-C₆)alkyl; and     m is zero.

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):

wherein U is O or S; and in (A): W is CH₂, CO or CHR¹⁹ wherein R¹⁹ is H, (C₁-C₆)alkyl or phenyl; R⁴ is H, (C₁-C₆)alkyl, phenyl, CH₂phenyl or OCH₂phenyl; R⁷ is H, (C₁-C₆)alkyl, (C₁-C₆)alkoxy or phenyl; and R⁸ is H or (C₁-C₆)alkyl; and in (C): Z is O; R⁴ is (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl or CH₂phenyl; and R⁹ and R¹⁰ are each H; and m is zero.

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

wherein U is NR¹⁸;

R² is H;

R³ is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₈)cycloalkyl; or is (C₁-C₆)alkyl substituted by one or two (C₁-C₆)alkoxy or CH[O(C₁-C₆)alkyl]₂ groups;

R⁴ and R¹⁸ are each the same or different H or (C₁-C₆)alkyl;

or R³ and R⁴ together with the adjacent N atom form a morpholin-1-yl or pyrazol-1-yl ring; and

m is zero.

A further preferred class of compounds of formula (I) are those in which:

R¹ is —C(═V)OR^(3a);

wherein V is O or S;

R² is H, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, NHCH₂phenyl; or is (C₁-C₆)alkyl substituted by a group selected from (C₁-C₆)alkoxy, CN, OH and S(O)_(n)R^(14a);

R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups are substituted by one or more R⁶ groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or substituted by one or more R⁶ groups; and

m is zero.

A more preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

R² is H;

U is O or S;

R³ is (C₁-C₆)alkoxy, C₁-C₆)haloalkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, CH₂phenyl or OCH₂phenyl, phenyl or 2-pyridyl which last four mentioned phenyl or pyridyl groups are unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN and NO2;

R⁴ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl; and

m is zero.

A further more preferred class of compounds of formula (I) are those in which:

R¹ is —C(═U)NR³R⁴;

R² is H;

U is O;

R³ is (C₁-C₆)alkoxy;

R⁴ is (C₁-C₆)alkyl; and

m is zero.

The compounds of general formula (I) can be prepared by the application or adaptation of known methods (i.e. methods heretofore used or described in the chemical literature.

In the following description of processes when symbols appearing in formulae are not specifically defined, it is understood that they are “as defined above” in accordance with the first definition of each symbol in the specification.

According to a feature of the invention compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, and R², U, R³ and R⁴ are as defined above; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, W, X, Y and Z are as defined above, may be prepared by the reaction of a compound of formula (II):

wherein L is a leaving group, generally halogen and preferably chlorine, with a compound of formula (III): HNR²—C(═U)NR³R⁴  (III) wherein R², U, R³ and R⁴ are as defined above, or with a compound of formula (IV), (V), (VI); (VII) or (VIII):

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, W, X, Y and Z are as defined above. The reaction is generally performed in the presence of an organic base such as a tertiary amine for example triethylamine, or pyridine, or an inorganic base such as an alkali metal carbonate, for example potassium carbonate, or an alkali metal alkoxide such as sodium ethoxide, or sodium hydride, in a solvent such as dioxan, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0° to 100° C. (preferably 0° to 50° C.).

According to a further feature of the present invention compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O, and R³ and R⁴ are as defined above, may be prepared by the reaction of a compound of formula (IX):

with oxalyl chloride or triphosgene, in an inert solvent such as dichloroethane at a temperature of from 0° C. to the reflux temperature of the solvent, followed by removal of the solvent to give the corresponding acylisocyanate intermediate which is generally not isolated, and which is directly reacted with an amine of formula (X): HNR³R⁴  (X) wherein R³ and R⁴ are as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds of formula (I) wherein R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O, and R^(3a) is as defined above, may be prepared by the reaction of a compound of formula (IX) as defined above, with oxalyl chloride to give an acylisocyanate intermediate above which is generally not isolated, and which is directly reacted with an alcohol of formula (XI): HOR^(3a)  (XI) wherein R³ is as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O or S, and R³ and R⁴ are as defined above, may be prepared by the reaction of a compound of formula (XII).

wherein U is O or S, with a compound of formula (X) as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds of formula (I) wherein R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O or S, and R^(3a) is as defined above, may be prepared by the reaction of a compound of formula (XIII).

wherein V is O or S, with a compound of formula (XI) as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds of formula (i) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, R⁴ is H, U is O or S, and R³ is as defined above, may be prepared by the reaction of a compound of formula (IX) as defined above, with a strong base such as sodium hydride to form the corresponding salt, which is then reacted with a compound of formula (XIV): R³N═C═U  (XIV) wherein R³ is as defined above. The reaction is generally performed in an inert solvent such as N,N-dimethylformamide at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a), m is zero, R² is H, U and V are each S, and R³, R^(3a) and R⁴ are as defined above, may be prepared in a 1-pot process by the reaction of 4-trifluoromethylnicotinic acid with a suitable halogenating agent, preferably oxalyl chloride, in a solvent such as dichloroethane, optionally in the presence of N,N-dimethylformamide, at a temperature of from 0° C. to the reflux temperature of the solvent, to give the corresponding acid chloride, followed by removal of the solvent, and reaction with an alkali metal thiocyanate or ammonium thiocyanate or a tetraalkylammonium thiocyanate for example tetrabutylammonium thiocyanate, generally in the presence of a base, such as an alkali metal carbonate for example potassium carbonate, in an inert solvent such as toluene or acetone, at a temperature of from 0° to 60° C., to give 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, followed by reaction with an amine of formula (X) above or an alcohol of formula (XI) above, at a temperature of from 0° to 60° C.

According to a further feature of the invention compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, U, R³ and R⁴ are as defined above, and R² is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which groups are unsubstituted or substituted by one or more R⁶ groups; or is —(CR¹⁵R¹⁶)_(p)aryl or —(CR¹⁵R¹⁶)_(p)heterocyclyl, which aryl or heterocyclyl groups are optionally substituted by R¹⁷; wherein R⁶, R¹⁵, R¹⁶ and R¹⁷ are as defined above, may be prepared by the reaction of the corresponding compound of formula (I) wherein R² is H, using an alkylatig agent of formula (XV): R²-L¹  (XV) wherein L¹ is a leaving group generally halogen and preferably chlorine. The reaction is generally performed in the presence of an organic base such as a tertiary amine for example triethylamine, or pyridine, or an inorganic base such as an alkali metal carbonate, for example potassium carbonate, or an alkali metal alkoxide such as sodium ethoxide, or sodium hydride, in a solvent such as dioxan, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0° to 100° C. (preferably 0° to 50° C.).

According to a further feature of the invention compounds of formula (I) wherein R¹, and R² are as defined above, and m is 1 may be prepared by oxidising a corresponding compound in which m is 0. The oxidation is generally performed using hydrogen peroxide in a solvent such as acetic acid, or a peracid such as 3-chloroperbenzoic acid in a solvent such as dichloromethane or 1,2-dichloroethane, at a temperature of from 0° C. to the reflux temperature of the solvent.

Intermediates of formula (II) wherein L is chlorine, may be prepared according to known procedures, for example by the reaction of the corresponding carboxylic acid of formula (II) wherein L is replaced by OH, with a suitable halogenating agent, preferably oxalyl chloride or thionyl chloride, in a solvent such as dichloroethane, optionally in the presence of N,N-dimethylformamide, at a temperature of from 0° C. to the reflux temperature of the solvent.

Intermediates of formula (XII) wherein U is S, and (XIII) wherein V is O, may be prepared according to known procedures, for example by the reaction of a compound of formula (II) as defined above, with an alkali metal thiocyanate or ammonium thiocyanate or a tetraalkylammonium thiocyanate for example tetrabutylammonium thiocyanate, generally in the presence of a base such as an alkali metal carbonate for example potassium carbonate, in an inert solvent solvent such as toluene or acetone, at a temperature of from 0° to 100° C.

Intermediate of formula (XII) wherein U is O, may be prepared according to known procedures, for example by the reaction of a compound of formula (II) as defined above, with an alkali metal cyanate or ammonium cyanate or a tetraalkylammonium cyanate for example tetrabutylammonium cyanate, generally in the presence of a base such as an alkali metal carbonate for example potassium carbonate, in an inert solvent solvent such as toluene, at a temperature of from 0° to 100° C.

Collections of compounds of the formula (I) which can be synthesized by the above mentioned process may also be prepared in a parallel manner, and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, work-up or purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, Volume 1, Verlag Escom 1997, pages 69 to 77.

A series of commercially available apparatuses as are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany or Radleys, Shirehill, Saffron Walden, Essex, England, may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those by ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations must be performed between the process steps. This can be prevented by employing semi-integrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

In addition to what has been described here, compounds of the formula (I) may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the “tea-bag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products by IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses by Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation of the processes described herein yields compounds of the formula (I) in the form of substance collections which are termed libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I).

Compounds of formula (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XIV) and (XV) are known or may be prepared by known methods.

The following non-limiting Examples illustrate the preparation of the compounds of formula (I).

CHEMICAL EXAMPLES

NMR spectra were run in deuterochloroform unless stated otherwise. In the Examples which follow, quantities (also percentages) are weight-based, unless stated otherwise.

Example 1

Oxalyl chloride (0.15 ml) was added to a suspension of 4-trifluoromethyl-3-pyridinecarboxamide (0.25 g) in 1,2-dichloroethane at 20° C. and then heated to reflux for 2 hours. The mixture was cooled, evaporated and the residue containing 4-trifluoromethyl-3-pyridylcarbonyl isocyanate was dissolved in tetrahydrofuran. Benzylamine (0.15 ml) was added and the mixture stirred at 20° C. for 2 hours and evaporated. The residue was purified by silica-gel column chromatography, eluting with n-hexane/ethyl acetate (3:2), to give 1-benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.30 g, Compound A-37).

By proceeding in a similar manner there was prepared 1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (Compound A-862).

Example 2

Oxalyl chloride (1.50 ml) was added to a suspension of 4-trifluoromethyl-3-pyridinecarboxamide (2.0 g) in 1,2-dichloroethane at 20° C., and stirred under reflux for 2 hours. The mixture was evaporated and dichloromethane added to the residue containing 4-trifluoromethyl-3-pyridylcarbonyl isocyanate. To this was added at 20° C. a suspension of N,O-dimethylhydroxylamine hydrochloride (2.05 g) and triethylamine (3.0 ml) in dichloromethane, which had been prepared in advance. The mixture was stirred for 30 minutes, then water added and the organic layer dried (magnesium sulfate) and evaporated, to give after trituration with ethanol, 1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (2.2 g) (Compound A-313).

By proceeding in a similar manner there was prepared 1-hydroxyl-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (Compound A-540).

Example 3

Sodium hydride (0.090 g, 60% dispersion in mineral oil) was added to a solution of 4-trifluoromethyl-3-pyridinecarboxamide (0.40 g) in N,N-dimethylformamide at 20° C., and stirred for 1 hour. Benzyl isocyanate (0.31 ml) was added and the mixture stirred at 20° C. for 2 hours, then methyl bromoacetate (0.30 ml) added and stirring continued for 5 hours. Ethyl acetate and water were added to the solution and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1), to give 3-benzyl-1-(4-trifluoromethyl-3-pyridylcarbonyl)hydantoin (0.50 g, Compound S-132).

Example 4

Methanesulfonyl chloride (0.17 ml) was added to an ice-cooled mixture of 1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.70 g), and triethylamine (0.64 ml) in dichloromethane, then stirred for 3 hours at 20° C. The mixture was washed (water), dried (magnesium sulfate), evaporated and the residue purified by silica-gel chromatography, eluting with n-hexane/ethyl acetate (3:2), to give 1-benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)-2-imidazolidinone (0.63 g, Compound S-15).

Example 5

1,2-Dibromoethane (0.06 ml) was added to a suspension of 1-hydroxyl-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.20 g) and potassium carbonate (0.20 g) in N,N-dimethylformamide at 20° C., and stirred for 3 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1), to give 2-isopropyl-4-(4-trifluoromethyl-3-pyridylcarbonyl)-perhydro-1,2,4-oxadiazin-3-one (0.25 g, Compound U-3).

Example 6

Oxalyl chloride (3.2 ml, 2M) was added to a suspension of 4-trifluoromethylnicotinic acid (1 g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1 hour. After evaporation, the residue was dissolved in acetone and potassium thiocyanate (1 g) added with ice bath cooling to give 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, then N-methylaniline (0.65 g) was added and the mixture stirred at 20° C. for 1 hour. Ethyl acetate was added and the mixture washed with water, dried (magnesium sulfate), evaporated and the residue purified by silica-gel chromatography, eluting with n-hexane/ethyl acetate=2/1, to give 1-methyl-1-phenyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)thiourea (0.96 g, Compound B-349).

Example 7

Oxalyl chloride (6.4 ml, 2M) was added to a suspension of 4-trifluoromethylnicotinic acid (2 g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1 hour to give a solution of 4-trifluoromethylnicotinic acid chloride. N,N-Ethylenethiourea (2.23 g) was added to sodium hydride (0.82 g, 60% dispersion in mineral oil) in tetrahydrofuran, and the mixture was stirred at 20° C. for 1 hour, and then added to the above solution of 4-trifluoromethylnicotinic acid chloride with ice bath cooling, then stirred at 20° C. for 1 hour. Ethyl acetate was added and the mixture washed with water, dried (magnesium sulfate), evaporated and the residue crystallized (ethanol) to give N-(4-trifluoromethyl-3-pyridylcarbonyl)-imidazolin-2-thione (1.35 g, Compound S-356).

Example 8

Oxalyl chloride (9.6 ml, 2M) was added to a suspension 4-trifluoromethylnicotinic acid (3 g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1 hour. The mixture was evaporated, the residue dissolved in toluene and tetrabutylammonium thiocyanate (3 g) and potassium carbonate (1.5 g) added, then stirred at 20° C. for 30 minutes to give 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate 2,2,2-trifluoroethanol (3.15 g) was then added, and the mixture stirred at 20° C. for 1 hour. Ethyl acetate was added and the mixture washed with water, hydrochloric acid 1(M), saturated sodium bicarbonate and brine, dried (magnesium sulfate), evaporated and recrystallised from ethanol to give 2,2,2-trifluoroethyl N-(4-trifluoromethyl-3-pyridylcarbonyl)thiocarbamate (1.2 g, Compound X-45).

Example 9

Allyl bromide (0.10 ml) was added to a suspension of 1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.25 g) and potassium carbonate (0.16 g) in N,N-dimethylformamide at 20° C., and stirred for 2 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1) to give 1-methyl-1-methoxy-3-allyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.26 g, Compound E-85).

The following preferred compounds shown in Tables 1 to 9 also form part of the present invention, and were or may be prepared in accordance with, or analogously to, the above-mentioned Examples 1 to 9 or the above-described general methods. In the Tables Ph means phenyl. Where subscripts are omitted after atoms it will be understood that they are intended, for example CH3 means CH₃.

Compound numbers are given for reference purposes only. TABLE I Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; R² is H and m is zero. In Table 1 compounds A-1 to A-881 represent individual compounds in which U is O, whilst compounds B-1 to B-881 represent individual compounds in which U is S. Compound R³ R⁴ A-1 B-1 CH₃CH═CH H A-2 B-2 CH₂═CHCH₂ H A-3 B-3 CH₃(CH₃)C═CH H A-4 B-4 (CH₃)₂C═CH H A-5 B-5 CH₃CH═CHCH₂ H A-6 B-6 CH₂═C(CH₃)CH₂ H A-7 B-7 CH₃CH═C(Cl)CH₂ H A-8 B-8 CH₂═CHCH₂CH₂ H A-9 B-9 CH₃CH₂(CH₃)C═CH H A-10 B-10 (CH₃)₂CHCH═CH H A-11 B-11 CH₂CH₂CH═CHCH₂ H A-12 B-12 CH₃CH═C(CH₃)CH₂ H A-13 B-13 CH(CH₃)HC═CHCH₃ H A-14 B-14 CH₂HC═C(CH₃)₂ H A-15 B-15 CH₃CH═CHCH₂CH₂ H A-16 B-16 CH₂═CH₂CH₂CH₂CH₂ H A-17 B-17 CH₂═CH₂CH₂CH₂CHCH₂ H A-18 B-18 CHCCH₂ H A-19 B-19 CH₃CCCH₂ H A-20 B-20 CHCCH(CH₃) H A-21 B-21 CH₃CCCH(CH₃) H A-22 B-22 CHCC(CH₃)₂ H A-23 B-23 CH₃CCC(CH₃)₂ H A-24 B-24 cyclo-C₃H₅ H A-25 B-25 cyclo-C₃H₄(₁-CH₃) H A-26 B-26 cyclo-C₄H7 H A-27 B-27 cyclo-C₄H6(₁-CH₃) H A-28 B-28 cyclo-C₅H9 H A-29 B-29 cyclo-C₅H8(₁-CH₃) H A-30 B-30 cyclo-C6H₁₁ H A-31 B-31 cyclo-C6H₁₀(₁-CH₃) H A-32 B-32 (cyclo-C₃H₅)CH₂ H A-33 B-33 (cyclo-C₃H₄(₁-CH₃))CH₂ H A-34 B-34 (cyclo-C₄H7)CH₂ H A-35 B-35 (cyclo-C₅H9)CH₂ H A-36 B-36 (cyclo-C6H₁₁)CH₂ H A-37 B-37 PhCH₂ H A-38 B-38 PhCH(CH₃) H A-39 B-39 PhCH₂CH₂ H A-40 B-40 PhC(CH₃)₂ H A-41 B-41 PhCH₂CH₂ H A-42 B-42 (2-F—Ph)CH₂ H A-43 B-43 (3-F—Ph)CH₂ H A-44 B-44 (4-F—Ph)CH₂ H A-45 B-45 (2-Cl—Ph)CH₂ H A-46 B-46 (3-Cl—Ph)CH₂ H A-47 B-47 (4-Cl—Ph)CH₂ H A-48 B-48 (2-Br—Ph)CH₂ H A-49 B-49 (3-Br—Ph)CH₂ H A-50 B-50 (4-Br—Ph)CH₂ H A-51 B-51 (2-I—Ph)CH₂ H A-52 B-52 (3-I—Ph)CH₂ H A-53 B-53 (4-I—Ph)CH₂ H A-54 B-54 (2-CF₃—Ph)CH₂ H A-55 B-55 (3-CF₃—Ph)CH₂ H A-56 B-56 (4-CF₃—Ph)CH₂ H A-57 B-57 (2-CH₃—Ph)CH₂ H A-58 B-58 (3-CH₃—Ph)CH₂ H A-59 B-59 (4-CH₃—Ph)CH₂ H A-60 B-60 (2-CH₃O—Ph)CH₂ H A-61 B-61 (3-CH₃O—Ph)CH₂ H A-62 B-62 (4-CH₃O—Ph)CH₂ H A-63 B-63 HO H A-64 B-64 CH₃O H A-65 B-65 CH₃CH₂O H A-66 B-66 n-C₃H7O H A-67 B-67 iso-C₃H7O H A-68 B-68 n-C₄H9O H A-69 B-69 sec-C₄H9O H A-70 B-70 iso-C₄H9O H A-71 B-71 tert-C₄H9O H A-72 B-72 n-C₅H₁₁O H A-73 B-73 n-C6H₁₃O H A-74 B-74 CH₂═CHCH₂O H A-75 B-75 CH₂═C(CH₃)CH₂O H A-76 B-76 CH₂═CHCH(CH₃)O H A-77 B-77 CH₂═C(Cl)CH₂O H A-78 B-78 CH₂═CHC(CH₃)₂O H A-79 B-79 CH₃CH═CHCH₂O H A-80 B-80 CH₂═CH₂CH₂CH₂O H A-81 B-81 CHCCH₂O H A-82 B-82 CH₃CCCH₂O H A-83 B-83 CHCCH(CH₃)O H A-84 B-84 CHCC(CH₃)₂O H A-85 B-85 CH₃CH₂O₂CCH₂O H A-86 B-86 PhCH₂O H A-87 B-87 2-CH₃O—PhCH₂O H A-88 B-88 3-CH₃O—PhCH₂O H A-89 B-89 4-CH₃O—PhCH₂O H A-90 B-90 PhO H A-91 B-91 2-Cl—PhO H A-92 B-92 3-Cl—PhO H A-93 B-93 4-Cl—PhO H A-94 B-94 2-CF₃—PhO H A-95 B-95 3-CF₃—PhO H A-96 B-96 4-CF₃—PhO H A-97 B-97 2-CH₃O—PhO H A-98 B-98 3-CH₃O—PhO H A-99 B-99 4-CH₃O—PhO H A-100 B-100 NH₂ H A-101 B-101 CH₃NH H A-102 B-102 C₂H₅NH H A-103 B-103 n-C₃H7NH H A-104 B-104 iso-C₃H7NH H A-105 B-105 n-C₄H9NH H A-106 B-106 n-C₅H₁₁NH H A-107 B-107 n-C6H₁₃NH H A-108 B-108 PhCH₂NH H A-109 B-109 PhNH H A-110 B-110 2-F—PhNH H A-111 B-111 3-F—PhNH H A-112 B-112 4-F—PhNH H A-113 B-113 2-Cl—PhNH H A-114 B-114 3-Cl—PhNH H A-115 B-115 4-Cl—PhNH H A-116 B-116 2-Br—PhNH H A-117 B-117 3-Br—PhNH H A-118 B-118 4-Br—PhNH H A-119 B-119 2-I—PhNH H A-120 B-120 3-I—PhNH H A-121 B-121 4-I—PhNH H A-122 B-122 2-CF₃—PhNH H A-123 B-123 3-CF₃—PhNH H A-124 B-124 4-CF₃—PhNH H A-125 B-125 2-CH₃—PhNH H A-126 B-126 3-CH₃—PhNH H A-127 B-127 4-CH₃—PhNH H A-128 B-128 2-CH₃O—PhNH H A-129 B-129 3-CH₃O—PhNH H A-130 6-130 4-CH₃O—PhNH H A-131 B-131 2-NO₂—PhNH H A-132 B-132 3-NO₂—PhNH H A-133 B-133 4-NO₂—PhNH H A-134 B-134 2-CN—PhNH H A-135 B-135 3-CN—PhNH H A-136 B-136 4-CN—PhNH H A-137 B-137 Ph(Me)N H A-138 B-138 2-F—Ph(Me)N H A-139 B-139 3-F—Ph(Me)N H A-140 B-140 4-F—Ph(Me)N H A-141 B-141 2-Cl—Ph(Me)N H A-142 B-142 3-Cl—Ph(Me)N H A-143 B-143 4-Cl—Ph(Me)N H A-144 B-144 3-CF₃—Ph(Me)N H A-145 B-145 4-CF₃—Ph(Me)N H A-146 B-146 2-CH₃O—Ph(Me)N H A-147 B-147 3-CH₃O—Ph(Me)N H A-148 B-148 4-CH₃O—Ph(Me)N H A-149 B-149 Ph H A-150 B-150 2-F—Ph H A-151 B-151 3-F—Ph H A-152 B-152 4-F—Ph H A-153 B-153 2-Cl—Ph H A-154 B-154 3-Cl—Ph H A-155 B-155 4-Cl—Ph H A-156 B-156 2-Br—Ph H A-157 B-157 3-Br—Ph H A-158 B-158 4-Br—Ph H A-159 B-159 2-I—Ph H A-160 B-160 3-I—Ph H A-161 B-161 4-I—Ph H A-162 B-162 2-CF₃—Ph H A-163 B-163 3-CF₃—Ph H A-164 B-164 4-CF₃—Ph H A-165 B-165 2-CH₃—Ph H A-166 B-166 3-CH₃—Ph H A-167 B-167 4-CH₃—Ph H A-168 B-168 2-CH₃O—Ph H A-169 B-169 3-CH₃O—Ph H A-170 B-170 4-CH₃O—Ph H A-171 B-171 2-NO₂—Ph H A-172 B-172 3-NO₂—Ph H A-173 B-173 4-NO₂—Ph H A-174 B-174 2-CN—Ph H A-175 B-175 3-CN—Ph H A-176 B-176 4-CN—Ph H A-177 B-177 2-CO₂H—Ph H A-178 B-178 3-CO₂H—Ph H A-179 B-179 4-CO₂H—Ph H A-180 B-180 2-CO₂Me—Ph H A-181 B-181 3-CO₂Me—Ph H A-182 B-182 4-CO₂Me—Ph H A-183 B-183 2-HO—Ph H A-184 B-184 3-HO—Ph H A-185 B-185 4-HO—Ph H A-186 B-186 2-NH₂—Ph H A-187 B-187 3-NH₂—Ph H A-188 B-188 4-NH₂—Ph H A-189 B-189 2-HOCH₂—Ph H A-190 B-190 3-HOCH₂—Ph H A-191 B-191 4-HOCH₂—Ph H A-192 B-192 2-CF₃O—Ph H A-193 B-193 3-CF₃O—Ph H A-194 B-194 4-CF₃O—Ph H A-195 B-195 2-CF₃CH₂O—Ph H A-196 B-196 3-CF₃CH₂O—Ph H A-197 B-197 4-CF₃CH₂O—Ph H A-198 B-198 2-(4-Cl—PhO)—Ph H A-199 B-199 3-(4-Cl—PhO)—Ph H A-200 B-200 4-(4-Cl—PhO)—Ph H A-201 B-201 2-(4-CF₃—PhO)—Ph H A-202 B-202 3-(4-CF₃—PhO)—Ph H A-203 B-203 4-(4-CF₃—PhO)—Ph H A-204 B-204 2,3-diCl—Ph H A-205 B-205 2,5-diCl—Ph H A-206 B-206 2,6-diCl—Ph H A-207 B-207 3,4-diCl—Ph H A-208 B-208 3,5-diCl—Ph H A-209 B-209 2-Pyridyl H A-210 B-210 3-Pyridyl H A-211 B-211 4-Pyridyl H A-212 B-212 2-Pyrimidyl H A-213 B-213 1-Pyrrolyl H A-214 B-214 1-Pyrazolyl H A-215 B-215 3-Pyrazolyl H A-216 B-216 1,2,4-Triazol-1-yl H A-217 B-217 1,2,4-Triazol-3-yl H A-218 B-218 2-Furanyl H A-219 B-219 3-Furanyl H A-220 B-220 2-Thienyl H A-221 B-221 3-Thienyl H A-222 B-222 2-Thiazolyl H A-223 B-223 1,3,4-Thiadiazol-2-yl H A-224 B-224 3-Isoxazolyl H A-225 B-225 CH₃CO H A-226 B-226 CH₃CH₂CO H A-227 B-227 n-C₃H7CO H A-228 B-228 iso-C₃H7CO H A-229 B-229 n-C₄H9CO H A-230 B-230 iso-C₄H9CO H A-231 B-231 sec-C₄H9CO H A-232 B-232 tert-C₄H9CO H A-233 B-233 n-C5H₁₁CO H A-234 B-234 n-C6H₁₂CO H A-235 B-235 PhCO H A-236 B-236 PhCH₂CO H A-237 B-237 CH₃SO₂ H A-238 B-238 C₂H5SO₂ H A-239 B-239 n-C₃H7SO₂ H A-240 B-240 iso-C₃H7SO₂ H A-241 B-241 PhCH₂SO₂ H A-242 B-242 PhSO₂ H A-243 B-243 2-Cl—PhSO₂ H A-244 B-244 3-Cl—PhSO₂ H A-245 B-245 4-Cl—PhSO₂ H A-246 B-246 CH₃SO₂NH H A-247 B-247 PhSO₂NH H A-248 B-248 CF₃CH₂ H A-249 B-249 ClCH₂CH₂ H A-250 B-250 ClCH₂CH₂CH₂ H A-251 B-251 CH₃OCH₂CH₂ H A-252 B-252 CH₃CH₂OCH₂CH₂ H A-253 B-253 CH₃OCH₂CH₂CH₂ H A-254 B-254 C₂H5OCH₂CH₂CH₂ H A-255 B-255 n-C₄H9OCH₂CH₂CH₂ H A-256 B-256 (CH₃O)₂CHCH₂ H A-257 B-257 CH₃CONH H A-258 B-258 PhCONH H A-259 B-259 Ph₂C═N H A-260 B-260 HOCH₂CH₂ H A-261 B-261 HOCH₂CH₂CH₂ H A-262 B-262 CH₃O₂CCH₂ H A-263 B-263 CH₃O₂CCH(CH₃) H A-264 B-264 CH₃O₂CC(CH₃)₂ H A-265 B-265 NCCH₂ H A-266 B-266 NCCH(CH₃) H A-267 B-267 NCC(CH₃)₂ H A-268 B-268 NC(CH₃)(iso-C₃H7)C H A-269 B-269 HOCH₂CH₂CH₂CH₂ H A-270 B-270 CHCCH₂O H A-271 B-271 CH₃O₂CCH₂O H A-272 B-272 CH₃O₂CCH(CH₃)O H A-273 B-273 CH₃O₂CC(CH₃)₂O H A-274 B-274 (1-pyrrolidinyl)CH₂CH₂ H A-275 B-275 CH₂═CHCH₂ CH₃ A-276 B-276 CH₃CH═CHCH₂ CH₃ A-277 B-277 CH₂═C(CH₃)CH₂ CH₃ A-278 B-278 CH₂═CH(CH₃)CH CH₃ A-279 B-279 CH₂═CHCH₂CH₂ CH₃ A-280 B-280 CH₃CH═C(CH₃)CH₂ CH₃ A-281 B-281 CH(CH₃)HC═CHCH₃ CH₃ A-282 B-282 C(CH₃)₂HC═CH₂ CH₃ A-283 B-283 CH₂HC═C(CH₃)₂ CH₃ A-284 B-284 CH₃CH═CHCH₂CH₂ CH₃ A-285 B-285 CH₂═CHCH₂CH₂CH₂ CH₃ A-286 B-286 CHCCH₂ CH₃ A-287 B-287 CH₃CCCH₂ CH₃ A-288 B-288 CHCCH(CH₃) CH₃ A-289 B-289 CH₃CCCH(CH₃) CH₃ A-290 B-290 cyclo-C₃H5 CH₃ A-291 B-291 cyclo-C5H9 CH₃ A-292 B-292 cyclo-C6H₁₁ CH₃ A-293 B-293 (cyclo-C₃H5)CH₂ CH₃ A-294 B-294 (cyclo-C5H9)CH₂ CH₃ A-295 B-295 (cyclo-C6H₁₁)CH₂ CH₃ A-296 B-296 PhCH₂ CH₃ A-297 B-297 PhCH(CH₃) CH₃ A-298 B-298 PhC(CH₃)₂ CH₃ A-299 B-299 PhCH₂CH₂ CH₃ A-300 B-300 (2-F—Ph)CH₂ CH₃ A-301 B-301 (3-F—Ph)CH₂ CH₃ A-302 B-302 (4-F—Ph)CH₂ CH₃ A-303 B-303 (2-Cl—Ph)CH₂ CH₃ A-304 B-304 (3-Cl—Ph)CH₂ CH₃ A-305 B-305 (4-Cl—Ph)CH₂ CH₃ A-306 B-306 (2-CF₃—Ph)CH₂ CH₃ A-307 B-307 (3-CF₃—Ph)CH₂ CH₃ A-308 B-308 (4-CF₃—Ph)CH₂ CH₃ A-309 B-309 (2-CH₃O—Ph)CH₂ CH₃ A-310 B-310 (3-CH₃O—Ph)CH₂ CH₃ A-311 B-311 (4-CH₃O—Ph)CH₂ CH₃ A-312 B-312 HO CH₃ A-313 B-313 CH₃O CH₃ A-314 B-314 CH₃CH₂O CH₃ A-315 B-315 n-C₃H7O CH₃ A-316 B-316 iso-C₃H7O CH₃ A-317 B-317 CH₂═CHCH₂O CH₃ A-318 B-318 CH₂═C(CH₃)CH₂O CH₃ A-319 B-319 CH₂═CHCH(CH₃)O CH₃ A-320 B-320 CH₂═CHCH(CH₃)O CH₃ A-321 B-321 CH₂═CHC(CH₃)₂O CH₃ A-322 B-322 CH₃CH═CHCH₂O CH₃ A-323 B-323 CHCCH₂O CH₃ A-324 B-324 CH₃CCCH₂O CH₃ A-325 B-325 CHCCH(CH₃)O CH₃ A-326 B-326 CH₃O₂CCH(CH₃)O CH₃ A-327 B-327 CH₃O₂CC(CH₃)₂O CH₃ A-328 B-328 CH₃O₂CCH₂O CH₃ A-329 B-329 PhCH₂O CH₃ A-330 B-330 PhO CH₃ A-331 B-331 NH₂ CH₃ A-332 B-332 CH₃NH CH₃ A-333 B-333 C₂H5NH CH₃ A-334 B-334 n-C₃H7NH CH₃ A-335 B-335 iso-C₃H7NH CH₃ A-336 B-336 PhCH₂NH CH₃ A-337 B-337 PhNH CH₃ A-338 B-338 2-F—PhNH CH₃ A-339 B-339 3-F—PhNH CH₃ A-340 B-340 4-F—PhNH CH₃ A-341 B-341 2-Cl—PhNH CH₃ A-342 B-342 3-Cl—PhNH CH₃ A-343 B-343 4-Cl—PhNH CH₃ A-344 B-344 2-CF₃—PhNH CH₃ A-345 B-345 3-CF₃—PhNH CH₃ A-346 B-346 2-CH₃O—PhNH CH₃ A-347 B-347 3-CH₃O—PhNH CH₃ A-348 B-348 4-CH₃O—PhNH CH₃ A-349 B-349 Ph CH₃ A-350 B-350 2-F—Ph CH₃ A-351 B-351 3-F—Ph CH₃ A-352 B-352 4-F—Ph CH₃ A-353 B-353 2-Cl—Ph CH₃ A-354 B-354 3-Cl—Ph CH₃ A-355 B-355 4-Cl—Ph CH₃ A-356 B-356 2-Br—Ph CH₃ A-357 B-357 3-Br—Ph CH₃ A-358 B-358 4-Br—Ph CH₃ A-359 B-359 2-I—Ph CH₃ A-360 B-360 3-I—Ph CH₃ A-361 B-361 4-I—Ph CH₃ A-362 B-362 2-CF₃—Ph CH₃ A-363 B-363 3-CF₃—Ph CH₃ A-364 B-364 4-CF₃—Ph CH₃ A-365 B-365 2-CH₃—Ph CH₃ A-366 B-366 3-CH₃—Ph CH₃ A-367 B-367 4-CH₃—Ph CH₃ A-368 B-368 2-CH₃O—Ph CH₃ A-369 B-369 3-CH₃O—Ph CH₃ A-370 B-370 4-CH₃O—Ph CH₃ A-371 B-371 2-NO₂—Ph CH₃ A-372 B-372 3-NO₂—Ph CH₃ A-373 B-373 4-NO₂—Ph CH₃ A-374 B-374 2-CN—Ph CH₃ A-375 B-375 3-CN—Ph CH₃ A-376 B-376 4-CN—Ph CH₃ A-377 B-377 2-CO₂Me—Ph CH₃ A-378 B-378 3-CO₂Me—Ph CH₃ A-379 B-379 4-CO₂Me—Ph CH₃ A-380 B-380 2-HO—Ph CH₃ A-381 B-381 3-HO—Ph CH₃ A-382 B-382 4-HO—Ph CH₃ A-383 B-383 2-NH₂—Ph CH₃ A-384 B-384 3-NH₂—Ph CH₃ A-385 B-385 4-NH₂—Ph CH₃ A-386 B-386 2-CF₃O—Ph CH₃ A-387 B-387 3-CF₃O—Ph CH₃ A-388 B-388 4-CF₃O—Ph CH₃ A-389 B-389 4-CF₃CH₂O—Ph CH₃ A-390 B-390 4-(4-Cl—PhO)—Ph CH₃ A-391 B-391 4-(4-CF₃—PhO)—Ph CH₃ A-392 B-392 2,3-diCl—Ph CH₃ A-393 B-393 2,4-diCl—Ph CH₃ A-394 B-394 2,5-diCl—Ph CH₃ A-395 B-395 2,6-diCl—Ph CH₃ A-396 B-396 3,4-diCl—Ph CH₃ A-397 B-397 3,5-diCl—Ph CH₃ A-398 B-398 2-Pyridyl CH₃ A-399 B-399 3-Pyridyl CH₃ A-400 B-400 4-Pyridyl CH₃ A-401 B-401 2-Pyrimidyl CH₃ A-402 B-402 1-Pyrrolyl CH₃ A-403 B-403 1-Pyrazolyl CH₃ A-404 B-404 3-Pyrazolyl CH₃ A-405 B-405 1,2,4-Triazol-1-yl CH₃ A-406 B-406 1,2,4-Triazol-3-yl CH₃ A-407 B-407 2-Furanyl CH₃ A-408 B-408 3-Furanyl CH₃ A-409 B-409 2-Thienyl CH₃ A-410 B-410 3-Thienyl CH₃ A-411 B-411 2-Thiazolyl CH₃ A-412 B-412 1,3,4-Thiadiazol-2-yl CH₃ A-413 B-413 3-Isoxazolyl CH₃ A-414 B-414 CH₃CO CH₃ A-415 B-415 PhCO CH₃ A-416 B-416 PhCH₂CO CH₃ A-417 B-417 CH₃SO₂NH CH₃ A-418 B-418 PhSO₂NH CH₃ A-419 B-419 CF₃CH₂ CH₃ A-420 B-420 ClCH₂CH₂ CH₃ A-421 B-421 ClCH₂CH₂CH₂ CH₃ A-422 B-422 CH₃OCH₂CH₂ CH₃ A-423 B-423 CH₃CH₂OCH₂CH₂ CH₃ A-424 B-424 CH₃OCH₂CH₂CH₂ CH₃ A-425 B-425 C₂H5OCH₂CH₂CH₂ CH₃ A-426 B-426 n-C₄H9OCH₂CH₂CH₂ CH₃ A-427 B-427 (CH₃O)₂CHCH₂ CH₃ A-428 B-428 CH₃CONH CH₃ A-429 B-429 PhCONH CH₃ A-430 B-430 Ph₂C═N CH₃ A-431 B-431 HOCH₂CH₂ CH₃ A-432 B-432 HOCH₂CH₂CH₂ CH₃ A-433 B-433 CH₃O₂CCH₂ CH₃ A-434 B-434 CH₃O₂CCH(CH₃) CH₃ A-435 B-435 CH₃O₂CC(CH₃)₂ CH₃ A-436 B-436 NCCH₂ CH₃ A-437 B-437 NC(CH₃)(iso-C₃H7)C CH₃ A-438 B-438 (1-pyrrolidinyl)CH₂CH₂ C₂H5 A-439 B-439 CH₂═CHCH₂ C₂H5 A-440 B-440 CHCCH₂ C₂H5 A-441 B-441 CH₃CCCH₂ C₂H5 A-442 B-442 (cyclo-C₃H5)CH₂ C₂H5 A-443 B-443 PhCH₂ C₂H5 A-444 B-444 PhCH₂CH₂ C₂H5 A-445 B-445 (2-Cl—Ph)CH₂ C₂H5 A-446 B-446 (3-Cl—Ph)CH₂ C₂H5 A-447 B-447 (4-Cl—Ph)CH₂ C₂H5 A-448 B-448 (2-CF₃—Ph)CH₂ C₂H5 A-449 B-449 (3-CF₃—Ph)CH₂ C₂H5 A-450 B-450 (4-CF₃—Ph)CH₂ C₂H5 A-451 B-451 (2-CH₃O—Ph)CH₂ C₂H5 A-452 B-452 (3-CH₃O—Ph)CH₂ C₂H5 A-453 B-453 (4-CH₃O—Ph)CH₂ C₂H5 A-454 B-454 HO C₂H5 A-455 B-455 CH₃O C₂H5 A-456 B-456 CH₃CH₂O C₂H5 A-457 B-457 n-C₃H7O C₂H5 A-458 B-458 iso-C₃H7O C₂H5 A-459 B-459 CH₂═CHCH₂O C₂H5 A-460 B-460 CHCCH₂O C₂H5 A-461 B-461 PhCH₂O C₂H5 A-462 B-462 PhO C₂H5 A-463 B-463 NH₂ C₂H5 A-464 B-464 CH₃NH C₂H5 A-465 B-465 C₂H5NH C₂H5 A-466 B-466 n-C₃H7NH C₂H5 A-467 B-467 iso-C₃H7NH C₂H5 A-468 B-468 PhCH₂NH C₂H5 A-469 B-469 PhNH C₂H5 A-470 B-470 2-Cl—PhNH C₂H5 A-471 B-471 3-Cl—PhNH C₂H5 A-472 B-472 4-Cl—PhNH C₂H5 A-473 B-473 2-CF₃—PhNH C₂H5 A-474 B-474 3-CF₃—PhNH C₂H5 A-475 B-475 2-CH₃O—PhNH C₂H5 A-476 B-476 3-CH₃O—PhNH C₂H5 A-477 B-477 4-CH₃O—PhNH C₂H5 A-478 B-478 Ph C₂H5 A-479 B-479 2-Cl—Ph C₂H5 A-480 B-480 3-Cl—Ph C₂H5 A-481 B-481 4-Cl—Ph C₂H5 A-482 B-482 2-CF₃—Ph C₂H5 A-483 B-483 3-CF₃—Ph C₂H5 A-484 B-484 4-CF₃—Ph C₂H5 A-485 B-485 2-CH₃O—Ph C₂H5 A-486 B-486 3-CH₃O—Ph C₂H5 A-487 B-487 4-CH₃O—Ph C₂H5 A-488 B-488 2-HO—Ph C₂H5 A-489 B-489 3-HO—Ph C₂H5 A-490 B-490 4-HO—Ph C₂H5 A-491 B-491 2-NH₂—Ph C₂H5 A-492 B-492 3-NH₂—Ph C₂H5 A-493 B-493 4-NH₂—Ph C₂H5 A-494 B-494 2-HOCH₂—Ph C₂H5 A-495 B-495 4-CF₃O—Ph C₂H5 A-496 B-496 4-CF₃CH₂O—Ph C₂H5 A-497 B-497 4-(4-Cl—PhO)—Ph C₂H5 A-498 B-498 4-(4-CF₃—PhO)—Ph C₂H5 A-499 B-499 2,3-diCl—Ph C₂H5 A-500 B-500 1-Pyrrolyl C₂H5 A-501 B-501 1-Pyrazolyl C₂H5 A-502 B-502 1,2,4-Triazol-1-yl C₂H5 A-503 B-503 2-Thiazolyl C₂H5 A-504 B-504 1,3,4-Thiadiazol-2-yl C₂H5 A-505 B-505 CH₃CO C₂H5 A-506 B-506 PhCO C₂H5 A-507 B-507 PhSO₂NH C₂H5 A-508 B-508 CF₃CH₂ C₂H5 A-509 B-509 ClCH₂CH₂ C₂H5 A-510 B-510 ClCH₂CH₂CH₂ C₂H5 A-511 B-511 CH₃OCH₂CH₂ C₂H5 A-512 B-512 CH₃CH₂OCH₂CH₂ C₂H5 A-513 B-513 CH₃OCH₂CH₂CH₂ C₂H5 A-514 B-514 C₂H5OCH₂CH₂CH₂ C₂H5 A-515 B-515 n-C₄H9OCH₂CH₂CH₂ C₂H5 A-516 B-516 (CH₃O)₂CHCH₂ C₂H5 A-517 B-517 CH₃CONH C₂H5 A-518 B-518 PhCONH C₂H5 A-519 B-519 HOCH₂CH₂ C₂H5 A-520 B-520 HOCH₂CH₂CH₂ C₂H5 A-521 B-521 CH₃O₂CCH₂ C₂H5 A-522 B-522 CH₃O₂CCH(CH₃) C₂H5 A-523 B-523 NCCH₂ n-C₃H7 A-524 B-524 HOCH₂CH₂ n-C₃H7 A-525 B-525 CH₂═CHCH₂ iso-C₃H7 A-526 B-526 CHCCH₂ iso-C₃H7 A-527 B-527 CH₃CCCH₂ iso-C₃H7 A-528 B-528 (cyclo-C₃H5)CH₂ iso-C₃H7 A-529 B-529 PhCH₂ iso-C₃H7 A-530 B-530 PhCH₂CH₂ iso-C₃H7 A-531 B-531 (2-Cl—Ph)CH₂ iso-C₃H7 A-532 B-532 (3-Cl—Ph)CH₂ iso-C₃H7 A-533 B-533 (4-Cl—Ph)CH₂ iso-C₃H7 A-534 B-534 (2-CF₃—Ph)CH₂ iso-C₃H7 A-535 B-535 (3-CF₃—Ph)CH₂ iso-C₃H7 A-536 B-536 (4-CF₃—Ph)CH₂ iso-C₃H7 A-537 B-537 (2-CH₃O—Ph)CH₂ iso-C₃H7 A-538 B-538 (3-CH₃O—Ph)CH₂ iso-C₃H7 A-539 B-539 (4-CH₃O—Ph)CH₂ iso-C₃H7 A-540 B-540 HO iso-C₃H7 A-541 B-541 CH₃O iso-C₃H7 A-542 B-542 CH₃CH₂O iso-C₃H7 A-543 B-543 n-C₃H7O iso-C₃H7 A-544 B-544 iso-C₃H7O iso-C₃H7 A-545 B-545 CH₂═CHCH₂O iso-C₃H7 A-546 B-546 CHCCH₂O iso-C₃H7 A-547 B-547 PhCH₂O iso-C₃H7 A-548 B-548 PhO iso-C₃H7 A-549 B-549 NH₂ iso-C₃H7 A-550 B-550 CH₃NH iso-C₃H7 A-551 B-551 C₂H5NH iso-C₃H7 A-552 B-552 n-C₃H7NH iso-C₃H7 A-553 B-553 iso-C₃H7NH iso-C₃H7 A-554 B-554 PhCH₂NH iso-C₃H7 A-555 B-555 PhNH iso-C₃H7 A-556 B-556 2-Cl—PhNH iso-C₃H7 A-557 B-557 3-Cl—PhNH iso-C₃H7 A-558 B-558 4-Cl—PhNH iso-C₃H7 A-559 B-559 2-CF₃—PhNH iso-C₃H7 A-560 B-560 3-CF₃—PhNH iso-C₃H7 A-561 B-561 2-CH₃O—PhNH iso-C₃H7 A-562 B-562 3-CH₃O—PhNH iso-C₃H7 A-563 B-563 4-CH₃O—PhNH iso-C₃H7 A-564 B-564 Ph iso-C₃H7 A-565 B-565 2-Cl—Ph iso-C₃H7 A-566 B-566 3-Cl—Ph iso-C₃H7 A-567 B-567 4-Cl—Ph iso-C₃H7 A-568 B-568 2-CF₃—Ph iso-C₃H7 A-569 B-569 3-CF₃—Ph iso-C₃H7 A-570 B-570 4-CF₃—Ph iso-C₃H7 A-571 B-571 2-CH₃O—Ph iso-C₃H7 A-572 B-572 3-CH₃O—Ph iso-C₃H7 A-573 B-573 4-CH₃O—Ph iso-C₃H7 A-574 B-574 2-HO—Ph iso-C₃H7 A-575 B-575 3-HO—Ph iso-C₃H7 A-576 B-576 4-HO—Ph iso-C₃H7 A-577 B-577 2-NH₂—Ph iso-C₃H7 A-578 B-578 3-NH₂—Ph iso-C₃H7 A-579 B-579 4-NH₂—Ph iso-C₃H7 A-580 B-580 2-HOCH₂—Ph iso-C₃H7 A-581 B-581 4-CF₃O—Ph iso-C₃H7 A-582 B-582 4-CF₃CH₂O—Ph iso-C₃H7 A-583 B-583 4-(4-Cl—PhO)—Ph iso-C₃H7 A-584 B-584 4-(4-CF₃—PhO)—Ph iso-C₃H7 A-585 B-585 2,3-diCl—Ph iso-C₃H7 A-586 B-586 1-Pyrrolyl iso-C₃H7 A-587 B-587 1-Pyrazolyl iso-C₃H7 A-588 B-588 1,2,4-Triazol-1-yl iso-C₃H7 A-589 B-589 2-Thiazolyl iso-C₃H7 A-590 B-590 1,3,4-Thiadiazol-₂-yl iso-C₃H7 A-591 B-591 CH₃CO iso-C₃H7 A-592 B-592 PhCO iso-C₃H7 A-593 B-593 PhSO₂NH iso-C₃H7 A-594 B-594 CF₃CH₂ iso-C₃H7 A-595 B-595 ClCH₂CH₂ iso-C₃H7 A-596 B-596 ClCH₂CH₂CH₂ iso-C₃H7 A-597 B-597 CH₃OCH₂CH₂ iso-C₃H7 A-598 B-598 CH₃CH₂OCH₂CH₂ iso-C₃H7 A-599 B-599 CH₃OCH₂CH₂CH₂ iso-C₃H7 A-600 B-600 C₂H5OCH₂CH₂CH₂ iso-C₃H7 A-601 B-601 n-C4H9OCH₂CH₂CH₂ iso-C₃H7 A-602 B-602 (CH₃O)₂CHCH₂ iso-C₃H7 A-603 B-603 CH₃CONH iso-C₃H7 A-604 B-604 PhCONH iso-C₃H7 A-605 B-605 HOCH₂CH₂ iso-C₃H7 A-606 B-606 HOCH₂CH₂CH₂ iso-C₃H7 A-607 B-607 CH₃O₂CCH₂ iso-C₃H7 A-608 B-608 CH₃O₂CCH(CH₃) iso-C₃H7 A-609 B-609 NCCH₂ iso-C₃H7 A-610 B-610 NC(CH₃)(iso-C₃H7) tert-C₄H9 A-611 B-611 CH₂═CHCH₂ tert-C₄H9 A-612 B-612 CHCCH₂ tert-C₄H9 A-613 B-613 CH₃CCCH₂ tert-C₄H₉ A-614 B-614 (cyclo-C₃H₅)CH₂ tert-C₄H₉ A-615 B-615 PhCH₂ tert-C₄H₉ A-616 B-616 PhCH₂CH₂ tert-C₄H₉ A-617 B-617 (2-Cl—Ph)CH₂ tert-C₄H₉ A-618 B-618 (3-Cl—Ph)CH₂ tert-C₄H₉ A-619 B-619 (4-Cl—Ph)CH₂ tert-C₄H₉ A-620 B-620 (2-CF₃—Ph)CH₂ tert-C₄H₉ A-621 B-621 (3-CF₃—Ph)CH₂ tert-C₄H₉ A-622 B-622 (4-CF₃—Ph)CH₂ tert-C₄H₉ A-623 B-623 (2-CH₃O—Ph)CH₂ tert-C₄H₉ A-624 B-624 (3-CH₃O—Ph)CH₂ tert-C₄H₉ A-625 B-625 (4-CH₃O—Ph)CH₂ tert-C₄H₉ A-626 B-626 HO tert-C₄H₉ A-627 B-627 CH₃O tert-C₄H₉ A-628 B-628 CH₃CH₂O tert-C₄H₉ A-629 B-629 n-C₃H7O tert-C₄H₉ A-630 B-630 iso-C₃H7O tert-C₄H₉ A-631 B-631 CH₂═CHCH₂O tert-C₄H₉ A-632 B-632 CHCCH₂O tert-C₄H₉ A-633 B-633 PhCH₂O tert-C₄H₉ A-634 B-634 PhO tert-C₄H₉ A-635 B-635 NH₂ tert-C₄H₉ A-636 B-636 CH₃NH tert-C₄H₉ A-637 B-637 C₂H5NH tert-C₄H₉ A-638 B-638 n-C₃H7NH tert-C₄H₉ A-639 B-639 iso-C₃H7NH tert-C₄H₉ A-640 B-640 PhCH₂NH tert-C₄H₉ A-641 B-641 PhNH tert-C₄H₉ A-642 B-642 2-Cl—PhNH tert-C₄H₉ A-643 B-643 3-Cl—PhNH tert-C₄H₉ A-644 B-644 ₄-Cl—PhNH tert-C₄H₉ A-645 B-645 2-CF₃—PhNH tert-C₄H₉ A-646 B-646 3-CF₃—PhNH tert-C₄H₉ A-647 B-647 2-CH₃O—PhNH tert-C₄H₉ A-648 B-648 3-CH₃O—PhNH tert-C₄H₉ A-649 B-649 4-CH₃O—PhNH tert-C₄H₉ A-650 B-650 Ph tert-C₄H₉ A-651 B-651 2-Cl—Ph tert-C₄H₉ A-652 B-652 3-Cl—Ph tert-C₄H₉ A-653 B-653 4-Cl—Ph tert-C₄H₉ A-654 B-654 2-CF₃—Ph tert-C₄H₉ A-655 B-655 3-CF₃—Ph tert-C₄H₉ A-656 B-656 4-CF₃—Ph tert-C₄H₉ A-657 B-657 2-CH₃O—Ph tert-C₄H₉ A-658 B-658 3-CH₃O—Ph tert-C₄H₉ A-659 B-659 4-CH₃O—Ph tert-C₄H₉ A-660 B-660 2-HO—Ph tert-C₄H₉ A-661 B-661 3-HO—Ph tert-C₄H₉ A-662 B-662 4-HO—Ph tert-C₄H₉ A-663 B-663 2-NH₂—Ph tert-C₄H₉ A-664 B-664 3-NH₂—Ph tert-C₄H₉ A-665 B-665 4-NH₂—Ph tert-C₄H₉ A-666 B-666 2-HOCH₂—Ph tert-C₄H₉ A-667 B-667 4-CF₃O—Ph tert-C₄H₉ A-668 B-668 4-CF₃CH₂O—Ph tert-C₄H₉ A-669 B-669 4-(4-Cl—PhO)—Ph tert-C₄H₉ A-670 B-670 4-(4-CF₃—PhO)—Ph tert-C₄H₉ A-671 B-671 2,3-diCl—Ph tert-C₄H₉ A-672 B-672 1-Pyrrolyl tert-C₄H₉ A-673 B-673 1-Pyrazolyl tert-C₄H₉ A-674 B-674 1,2,4-Triazol-1-yl tert-C₄H₉ A-675 B-675 2-Thiazolyl tert-C₄H₉ A-676 B-676 1,3,4-Thiadiazol-2-yl tert-C₄H₉ A-677 B-677 CH₃CO tert-C₄H₉ A-678 B-678 PhCO tert-C₄H₉ A-679 B-679 PhSO₂NH tert-C₄H₉ A-680 B-680 CF₃CH₂ tert-C₄H₉ A-681 B-681 ClCH₂CH₂ tert-C₄H₉ A-682 B-682 ClCH₂CH₂CH₂ tert-C₄H₉ A-683 B-683 CH₃OCH₂CH₂ tert-C₄H₉ A-684 B-684 CH₃CH₂OCH₂CH₂ tert-C₄H₉ A-685 B-685 CH₃OCH₂CH₂CH₂ tert-C₄H₉ A-686 B-686 C₂H5OCH₂CH₂CH₂ tert-C₄H₉ A-687 B-687 n-C₄H9OCH₂CH₂CH₂ tert-C₄H₉ A-688 B-688 (CH₃O)₂CHCH₂ tert-C₄H₉ A-689 B-689 CH₃CONH tert-C₄H₉ A-690 B-690 PhCONH tert-C₄H₉ A-691 B-691 HOCH₂CH₂ tert-C₄H₉ A-692 B-692 HOCH₂CH₂CH₂ tert-C₄H₉ A-693 B-693 CH₃O₂CCH₂ tert-C₄H₉ A-694 B-694 CH₃O₂CCH(CH₃) tert-C₄H₉ A-695 B-695 NCCH₂ tert-C₄H₉ A-696 B-696 NC(CH₃)(iso-C₃H7)C CH₂═CHCH₂ A-697 B-697 CH₂═CHCH₂ CH₂═CHCH₂ A-698 B-698 CHCCH₂ CH₂═CHCH₂ A-699 B-699 CH₃CCCH₂ CH₂═CHCH₂ A-700 B-700 (cyclo-C₃H5)CH₂ CH₂═CHCH₂ A-701 B-701 PhCH₂ CH₂═CHCH₂ A-702 B-702 PhCH₂CH₂ CH₂═CHCH₂ A-703 B-703 (2-Cl—Ph)CH₂ CH₂═CHCH₂ A-704 B-704 (3-Cl—Ph)CH₂ CH₂═CHCH₂ A-705 B-705 (4-Cl—Ph)CH₂ CH₂═CHCH₂ A-706 B-706 (2-CF₃—Ph)CH₂ CH₂═CHCH₂ A-707 B-707 (3-CF₃—Ph)CH₂ CH₂═CHCH₂ A-708 B-708 (4-CF₃—Ph)CH₂ CH₂═CHCH₂ A-709 B-709 (2-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-710 B-710 (3-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-711 B-711 (4-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-712 B-712 HO CH₂═CHCH₂ A-713 B-713 CH₃O CH₂═CHCH₂ A-714 B-714 CH₃CH₂O CH₂═CHCH₂ A-715 B-715 n-C₃H7O CH₂═CHCH₂ A-716 B-716 iso-C₃H7O CH₂═CHCH₂ A-717 B-717 CH₂═CHCH₂O CH₂═CHCH₂ A-718 B-718 CHCCH₂O CH₂═CHCH₂ A-719 B-719 PhCH₂O CH₂═CHCH₂ A-720 B-720 PhO CH₂═CHCH₂ A-721 B-721 NH₂ CH₂═CHCH₂ A-722 B-722 CH₃NH CH₂═CHCH₂ A-723 B-723 C₂H5NH CH₂═CHCH₂ A-724 B-724 n-C₃H7NH CH₂═CHCH₂ A-725 B-725 iso-C₃H7NH CH₂═CHCH₂ A-726 B-726 PhCH₂NH CH₂═CHCH₂ A-727 B-727 PhNH CH₂═CHCH₂ A-728 B-728 2-Cl—PhNH CH₂═CHCH₂ A-729 B-729 3-Cl—PhNH CH₂═CHCH₂ A-730 B-730 4-Cl—PhNH CH₂═CHCH₂ A-731 B-731 2-CF₃—PhNH CH₂═CHCH₂ A-732 B-732 3-CF₃—PhNH CH₂═CHCH₂ A-733 B-733 2-CH₃O—PhNH CH₂═CHCH₂ A-734 B-734 3-CH₃O—PhNH CH₂═CHCH₂ A-735 B-735 4-CH₃O—PhNH CH₂═CHCH₂ A-736 B-736 Ph CH₂═CHCH₂ A-737 B-737 2-Cl—Ph CH₂═CHCH₂ A-738 B-738 3-Cl—Ph CH₂═CHCH₂ A-739 B-739 4-Cl—Ph CH₂═CHCH₂ A-740 B-740 2-CF₃—Ph CH₂═CHCH₂ A-741 B-741 3-CF₃—Ph CH₂═CHCH₂ A-742 B-742 4-CF₃—Ph CH₂═CHCH₂ A-743 B-743 2-CH₃O—Ph CH₂═CHCH₂ A-744 B-744 3-CH₃O—Ph CH₂═CHCH₂ A-745 B-745 4-CH₃O—Ph CH₂═CHCH₂ A-746 B-746 2-HO—Ph CH₂═CHCH₂ A-747 B-747 3-HO—Ph CH₂═CHCH₂ A-748 B-748 4-HO—Ph CH₂═CHCH₂ A-749 B-749 2-NH₂—Ph CH₂═CHCH₂ A-750 B-750 3-NH₂—Ph CH₂═CHCH₂ A-751 B-751 4-NH₂—Ph CH₂═CHCH₂ A-752 B-752 2-HOCH₂—Ph CH₂═CHCH₂ A-753 B-753 4-CF₃O—Ph CH₂═CHCH₂ A-754 B-754 4-CF₃CH₂O—Ph CH₂═CHCH₂ A-755 B-755 4-(4-Cl—PhO)—Ph CH₂═CHCH₂ A-756 B-756 4-(4-CF₃—PhO)—Ph CH₂═CHCH₂ A-757 B-757 2,3-diCl—Ph CH₂═CHCH₂ A-758 B-758 1-Pyrrolyl CH₂═CHCH₂ A-759 B-759 1-Pyrazolyl CH₂═CHCH₂ A-760 B-760 1,2,4-Triazol-1-yl CH₂═CHCH₂ A-761 B-761 2-Thiazolyl CH₂═CHCH₂ A-762 B-762 1,3,4-Thiadiazol-2-yl CH₂═CHCH₂ A-763 B-763 CH₃CO CH₂═CHCH₂ A-764 B-764 PhCO CH₂═CHCH₂ A-765 B-765 PhSO₂NH CH₂═CHCH₂ A-766 B-766 CF₃CH₂ CH₂═CHCH₂ A-767 B-767 ClCH₂CH₂ CH₂═CHCH₂ A-768 B-768 ClCH₂CH₂CH₂ CH₂═CHCH₂ A-769 B-769 CH₃OCH₂CH₂ CH₂═CHCH₂ A-770 B-770 CH₃CH₂OCH₂CH₂ CH₂═CHCH₂ A-771 B-771 CH₃OCH₂CH₂CH₂ CH₂═CHCH₂ A-772 B-772 C₂H5OCH₂CH₂CH₂ CH₂═CHCH₂ A-773 B-773 n-C4H9OCH₂CH₂CH₂ CH₂═CHCH₂ A-774 B-774 (CH₃O)₂CHCH₂ CH₂═CHCH₂ A-775 B-775 CH₃CONH CH₂═CHCH₂ A-776 B-776 PhCONH CH₂═CHCH₂ A-777 B-777 HOCH₂CH₂ CH₂═CHCH₂ A-778 B-778 HOCH₂CH₂CH₂ CH₂═CHCH₂ A-779 B-779 CH₃O₂CCH₂ CH₂═CHCH₂ A-780 B-780 CH₃O₂CCH(CH₃) CH₂═CHCH₂ A-781 B-781 NCCH₂ CH₂═CHCH₂ A-782 B-782 NC(CH₃)(iso-C₃H7)C PhCH₂ A-783 B-783 CH₂═CHCH₂ PhCH₂ A-784 B-784 CHCCH₂ PhCH₂ A-785 B-785 CH₃CCCH₂ PhCH₂ A-786 B-786 (cyclo-C₃H5)CH₂ PhCH₂ A-787 B-787 PhCH₂ PhCH₂ A-788 B-788 PhCH₂CH₂ PhCH₂ A-789 B-789 (2-Cl—Ph)CH₂ PhCH₂ A-790 B-790 (3-Cl—Ph)CH₂ PhCH₂ A-791 B-791 (4-Cl—Ph)CH₂ PhCH₂ A-792 B-792 (2-CF₃—Ph)CH₂ PhCH₂ A-793 B-793 (3-CF₃—Ph)CH₂ PhCH₂ A-794 B-794 (4-CF₃—Ph)CH₂ PhCH₂ A-795 B-795 (2-CH₃O—Ph)CH₂ PhCH₂ A-796 B-796 (3-CH₃O—Ph)CH₂ PhCH₂ A-797 B-797 (4-CH₃O—Ph)CH₂ PhCH₂ A-798 B-798 HO PhCH₂ A-799 B-799 CH₃O PhCH₂ A-800 B-800 CH₃CH₂O PhCH₂ A-801 B-801 n-C₃H7O PhCH₂ A-802 B-802 iso-C₃H7O PhCH₂ A-803 B-803 CH₂═CHCH₂O PhCH₂ A-804 B-804 CHCCH₂O PhCH₂ A-805 B-805 PhCH₂O PhCH₂ A-806 B-806 PhO PhCH₂ A-807 B-807 NH₂ PhCH₂ A-808 B-808 CH₃NH PhCH₂ A-809 B-809 C₂H5NH PhCH₂ A-810 B-810 n-C₃H7NH PhCH₂ A-811 B-811 iso-C₃H7NH PhCH₂ A-812 B-812 PhCH₂NH PhCH₂ A-813 B-813 PhNH PhCH₂ A-814 B-814 2-Cl—PhNH PhCH₂ A-815 B-815 3-Cl—PhNH PhCH₂ A-816 B-816 4-Cl—PhNH PhCH₂ A-817 B-817 2-CF₃—PhNH PhCH₂ A-818 B-818 3-CF₃—PhNH PhCH₂ A-819 B-819 2-CH₃O—PhNH PhCH₂ A-820 B-820 3-CH₃O—PhNH PhCH₂ A-821 B-821 4-CH₃O—PhNH PhCH₂ A-822 B-822 Ph PhCH₂ A-823 B-823 2-Cl—Ph PhCH₂ A-824 B-824 3-Cl—Ph PhCH₂ A-825 B-825 4-Cl—Ph PhCH₂ A-826 B-826 2-CF₃—Ph PhCH₂ A-827 B-827 3-CF₃—Ph PhCH₂ A-828 B-828 4-CF₃—Ph PhCH₂ A-829 B-829 2-CH₃O—Ph PhCH₂ A-830 B-830 3-CH₃O—Ph PhCH₂ A-831 B-831 4-CH₃O—Ph PhCH₂ A-832 B-832 2-HO—Ph PhCH₂ A-833 B-833 3-HO—Ph PhCH₂ A-834 B-834 4-HO—Ph PhCH₂ A-835 B-835 2-NH₂—Ph PhCH₂ A-836 B-836 3-NH₂—Ph PhCH₂ A-837 B-837 4-NH₂—Ph PhCH₂ A-838 B-838 2-HOCH₂—Ph PhCH₂ A-839 B-839 4-CF₃O—Ph PhCH₂ A-840 B-840 4-CF₃CH₂O—Ph PhCH₂ A-841 B-841 4-(4-Cl—PhO)—Ph PhCH₂ A-842 B-842 4-(4-CF₃—PhO)—Ph PhCH₂ A-843 B-843 2,3-diCl—Ph PhCH₂ A-844 B-844 1-Pyrrolyl PhCH₂ A-845 B-845 1-Pyrazolyl PhCH₂ A-846 B-846 1,2,4-Triazol-1-yl PhCH₂ A-847 B-847 2-Thiazolyl PhCH₂ A-848 B-848 1,3,4-Thiadiazol-2-yl PhCH₂ A-849 B-849 CH₃CO PhCH₂ A-850 B-850 PhCO PhCH₂ A-851 B-851 PhSO₂NH PhCH₂ A-852 B-852 CF₃CH₂ PhCH₂ A-853 B-853 ClCH₂CH₂ PhCH₂ A-854 B-854 ClCH₂CH₂CH₂ PhCH₂ A-855 B-855 CH₃OCH₂CH₂ PhCH₂ A-856 B-856 CH₃CH₂OCH₂CH₂ PhCH₂ A-857 B-857 CH₃OCH₂CH₂CH₂ PhCH₂ A-858 B-858 C₂H5OCH₂CH₂CH₂ PhCH₂ A-859 B-859 n-C₄H9OCH₂CH₂CH₂ PhCH₂ A-860 B-860 (CH₃O)₂CHCH₂ PhCH₂ A-861 B-861 CH(CH₃)CH₂CH₂CH₂CH₂ A-862 B-862 HOCH₂CH₂ PhCH₂ A-863 B-863 CH₂CHBrCH₂CH₂ A-864 B-864 CH₂CH(OH)CH₂CH₂ A-865 B-865 CH₂CH═CHCH₂ A-866 B-866 benzothiazol-2-yl H A-867 B-867 Ph Ph A-868 B-868 CH₃CONH Ph A-869 B-869 HOCH₂CH₂ Ph A-870 B-870 CH₃SO₂OCH₂CH₂CH₂CH₂ H A-871 B-871 CH₂CH₂CH₂CH₂ A-872 B-872 CH₂CH₂CH₂CH₂CH₂ A-873 B-873 CH₂CH₂OCH₂CH₂ A-874 B-874 CH₂CH₂SCH₂CH₂ A-875 B-875 CH₂CH₂NHCH₂CH₂ A-876 B-876 CH₂CH₂N(CH₃)CH₂CH₂ A-877 B-877 N═CHCH₂CH₂ A-878 B-878 Ph NH₂ A-879 B-879 PhCH₂ (CH₃)₂C═N A-880 B-880 Ph (CH₃)₂C═N A-881 B-881 PhCH₂ H

TABLE 2 Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; U is O, m is zero and R² is as defined hereafter. In Table 2 compounds C-1 to C-151 represent individual compounds in which R² is methyl; compounds D-1 to D-151 represent individual compounds in which R² is ethyl; compounds E-1 to E-151 represent individual compounds in which R² is allyl; compounds F-1 to F-151 represent individual compounds in which R² is propargyl; compounds G-1 to G-151 represent individual compounds in which R² is benzyl; compounds H-1 to H-151 represent individual compounds in which R² is —CH₂CO₂CH₃; compounds I-1 to I-151 represent individual compounds in which R² is —CH(CH₃)CO₂CH₃; compounds J-1 to J-151 represent individual compounds in which R² is —CH₂CH(OCH₃)₂. Compound R³ R⁴ C-1 D-1 E-1 F-1 G-1 H-1 I-1 J-1 CH2═CHCH2 H C-2 D-2 E-2 F-2 G-2 H-2 I-2 J-2 CH3CH═CHCH2 H C-3 D-3 E-3 F-3 G-3 H-3 I-3 J-3 CH2═CHCH2CH2 H C-4 D-4 E-4 F-4 G-4 H-4 I-4 J-4 CHCCH2 H C-5 D-5 E-5 F-5 G-5 H-5 I-5 J-5 CH3CCCH2 H C-6 D-6 E-6 F-6 G-6 H-6 I-6 J-6 CHCCH(CH3) H C-7 D-7 E-7 F-7 G-7 H-7 I-7 J-7 cyclo-C3H5 H C-8 D-8 E-8 F-8 G-8 H-8 I-8 J-8 cyclo-C5H9 H C-9 D-9 E-9 F-9 G-9 H-9 I-9 J-9 cyclo-C6H11 H C-10 D-10 E-10 F-10 G-10 H-10 I-10 J-10 PhCH2 H C-11 D-11 E-11 F-11 G-11 H-11 I-11 J-11 PhCH(CH3) H C-12 D-12 E-12 F-12 G-12 H-12 I-12 J-12 NH2 H C-13 D-13 E-13 F-13 G-13 H-13 I-13 J-13 CH3NH H C-14 D-14 E-14 F-14 G-14 H-14 I-14 J-14 C2H5NH H C-15 D-15 E-15 F-15 G-15 H-15 I-15 J-15 n-C3H7NH H C-16 D-16 E-16 F-16 G-16 H-16 I-16 J-16 iso-C3H7NH H C-17 D-17 E-17 F-17 G-17 H-17 I-17 J-17 n-C4H9NH H C-18 D-18 E-18 F-18 G-18 H-18 I-18 J-18 tert-C4H9NH H C-19 D-19 E-19 F-19 G-19 H-19 I-19 J-19 n-C5H11NH H C-20 D-20 E-20 F-20 G-20 H-20 I-20 J-20 n-C6H13NH H C-21 D-21 E-21 F-21 G-21 H-21 I-21 J-21 PhCH2NH H C-22 D-22 E-22 F-22 G-22 H-22 I-22 J-22 PhNH H C-23 D-23 E-23 F-23 G-23 H-23 I-23 J-23 HO H C-24 D-24 E-24 F-24 G-24 H-24 I-24 J-24 CH3O H C-25 D-25 E-25 F-25 G-25 H-25 I-25 J-25 C2H5O H C-26 D-26 E-26 F-26 G-26 H-26 I-26 J-26 n-C3H7O H C-27 D-27 E-27 F-27 G-27 H-27 I-27 J-27 iso-C3H7O H C-28 D-28 E-28 F-28 G-28 H-28 I-28 J-28 n-C4H9O H C-29 D-29 E-29 F-29 G-29 H-29 I-29 J-29 tert-C4H9O H C-30 D-30 E-30 F-30 G-30 H-30 I-30 J-30 CH2═CHCH2O H C-31 D-31 E-31 F-31 G-31 H-31 I-31 J-31 CHCCH2O H C-32 D-32 E-32 F-32 G-32 H-32 I-32 J-32 CH3O2CCH2O H C-33 D-33 E-33 F-33 G-33 H-33 I-33 J-33 CH3O2CCH(CH3)O H C-34 D-34 E-34 F-34 G-34 H-34 I-34 J-34 CH3O2CC(CH3)2O H C-35 D-35 E-35 F-35 G-35 H-35 I-35 J-35 PhCH2O H C-36 D-36 E-36 F-36 G-36 H-36 I-36 J-36 Ph H C-37 D-37 E-37 F-37 G-37 H-37 I-37 J-37 2-F—Ph H C-38 D-38 E-38 F-38 G-38 H-38 I-38 J-38 3-F—Ph H C-39 D-39 E-39 F-39 G-39 H-39 I-39 J-39 4-F—Ph H C-40 D-40 E-40 F-40 G-40 H-40 I-40 J-40 2-Cl—Ph H C-41 D-41 E-41 F-41 G-41 H-41 I-41 J-41 3-Cl—Ph H C-42 D-42 E-42 F-42 G-42 H-42 I-42 J-42 4-Cl—Ph H C-43 D-43 E-43 F-43 G-43 H-43 I-43 J-43 2-CF3—Ph H C-44 D-44 E-44 F-44 G-44 H-44 I-44 J-44 3-CF3—Ph H C-45 D-45 E-45 F-45 G-45 H-45 I-45 J-45 4-CF3—Ph H C-46 D-46 E-46 F-46 G-46 H-46 I-46 J-46 2-CH3—Ph H C-47 D-47 E-47 F-47 G-47 H-47 I-47 J-47 3-CH3—Ph H C-48 D-48 E-48 F-48 G-48 H-48 I-48 J-48 4-CH3—Ph H C-49 D-49 E-49 F-49 G-49 H-49 I-49 J-49 2-CH3O—Ph H C-50 D-50 E-50 F-50 G-50 H-50 I-50 J-50 3-CH3O—Ph H C-51 D-51 E-51 F-51 G-51 H-51 I-51 J-51 4-CH3O—Ph H C-52 D-52 E-52 F-52 G-52 H-52 I-52 J-52 4-CF3O—Ph H C-53 D-53 E-53 F-53 G-53 H-53 I-53 J-53 4-CF3CH2O—Ph H C-54 D-54 E-54 F-54 G-54 H-54 I-54 J-54 4-PhO—Ph H C-55 D-55 E-55 F-55 G-55 H-55 I-55 J-55 4-(4-Cl—PhO)-Ph H C-56 D-56 E-56 F-56 G-56 H-56 I-56 J-56 4-(4-CF3—PhO)-Ph H C-57 D-57 E-57 F-57 G-57 H-57 I-57 J-57 CF3CH2 H C-58 D-58 E-58 F-58 G-58 H-58 I-58 J-58 ClCH2CH2 H C-59 D-59 E-59 F-59 G-59 H-59 I-59 J-59 ClCH2CH2CH2 H C-60 D-60 E-60 F-60 G-60 H-60 I-60 J-60 CH3OCH2CH2 H C-61 D-61 E-61 F-61 G-61 H-61 I-61 J-61 CH3CH2OCH2CH2 H C-62 D-62 E-62 F-62 G-62 H-62 I-62 J-62 CH3OCH2CH2CH2 H C-63 D-63 E-63 F-63 G-63 H-63 I-63 J-63 C2H5OCH2CH2CH2 H C-64 D-64 E-64 F-64 G-64 H-64 I-64 J-64 n-C4H9OCH2CH2CH2 H C-65 D-65 E-65 F-65 G-65 H-65 I-65 J-65 CH3OCH(CH3)CH2CH2 H C-66 D-66 E-66 F-66 G-66 H-66 I-66 J-66 (CH3O)2CHCH2 H C-67 D-67 E-67 F-67 G-67 H-67 I-67 J-67 HOCH2CH2 H C-68 D-68 E-68 F-68 G-68 H-68 I-68 J-68 HOCH2CH2CH2 H C-69 D-69 E-69 F-69 G-69 H-69 I-69 J-69 CH3SCH2CH2 H C-70 D-70 E-70 F-70 G-70 H-70 I-70 J-70 CH3CH2SCH2CH2 H C-71 D-71 E-71 F-71 G-71 H-71 I-71 J-71 CH3SCH2CH2CH2 H C-72 D-72 E-72 F-72 G-72 H-72 I-72 J-72 C2H5SCH2CH2CH2 H C-73 D-73 E-73 F-73 G-73 H-73 I-73 J-73 CH2═CHCH2 CH3 C-74 D-74 E-74 F-74 G-74 H-74 I-74 J-74 CHCCH2 CH3 C-75 D-75 E-75 F-75 G-75 H-75 I-75 J-75 cyclo-C3H5 CH3 C-76 D-76 E-76 F-76 G-76 H-76 I-76 J-76 cyclo-C5H9 CH3 C-77 D-77 E-77 F-77 G-77 H-77 I-77 J-77 cyclo-C6H11 CH3 C-78 D-78 E-78 F-78 G-78 H-78 I-78 J-78 PhCH2 CH3 C-79 D-79 E-79 F-79 G-79 H-79 I-79 J-79 NH2 CH3 C-80 D-80 E-80 F-80 G-80 H-80 I-80 J-80 CH3NH CH3 C-81 D-81 E-81 F-81 G-81 H-81 I-81 J-81 C2H5NH CH3 C-82 D-82 E-82 F-82 G-82 H-82 I-82 J-82 PhCH2NH CH3 C-83 D-83 E-83 F-83 G-83 H-83 I-83 J-83 PhNH CH3 C-84 D-84 E-84 F-84 G-84 H-84 I-84 J-84 HO CH3 C-85 D-85 E-85 F-85 G-85 H-85 I-85 J-85 CH3O CH3 C-86 D-86 E-86 F-86 G-86 H-86 I-86 J-86 C2H5O CH3 C-87 D-87 E-87 F-87 G-87 H-87 I-87 J-87 CH2═CHCH2O CH3 C-88 D-88 E-88 F-88 G-88 H-88 I-88 J-88 CHCCH2O CH3 C-89 D-89 E-89 F-89 G-89 H-89 I-89 J-89 CH3O2CCH2O CH3 C-90 D-90 E-90 F-90 G-90 H-90 I-90 J-90 CH3O2CCH(CH3)O CH3 C-91 D-91 E-91 F-91 G-91 H-91 I-91 J-91 PhCH2O CH3 C-92 D-92 E-92 F-92 G-92 H-92 I-92 J-92 Ph CH3 C-93 D-93 E-93 F-93 G-93 H-93 I-93 J-93 4-CF3O—Ph CH3 C-94 D-94 E-94 F-94 G-94 H-94 I-94 J-94 4-(4-CF3O)-Ph CH3 C-95 D-95 E-95 F-95 G-95 H-95 I-95 J-95 CF3CH2 CH3 C-96 D-96 E-96 F-96 G-96 H-96 I-96 J-96 CH3OCH2CH2 CH3 C-97 D-97 E-97 F-97 G-97 H-97 I-97 J-97 CH3CH2OCH2CH2 CH3 C-98 D-98 E-98 F-98 G-98 H-98 I-98 J-98 CH3OCH2CH2CH2 CH3 C-99 D-99 E-99 F-99 G-99 H-99 I-99 J-99 C2H5OCH2CH2CH2 CH3 C-100 D-100 E-100 F-100 G-100 H-100 I-100 J-100 n-C4H9OCH2CH2CH2 CH3 C-101 D-101 E-101 F-101 G-101 H-101 I-101 J-101 (CH3O)2CHCH2 CH3 C-102 D-102 E-102 F-102 G-102 H-102 I-102 J-102 HOCH2CH2 CH3 C-103 D-103 E-103 F-103 G-103 H-103 I-103 J-103 HOCH2CH2CH2 CH3 C-104 D-104 E-104 F-104 G-104 H-104 I-104 J-104 CH3OCH2CH2CH2 CH3 C-105 D-105 E-105 F-105 G-105 H-105 I-105 J-105 C2H5OCH2CH2CH2 CH3 C-106 D-106 E-106 F-106 G-106 H-106 I-106 J-106 n-C4H9OCH2CH2CH2 CH3 C-107 D-107 E-107 F-107 G-107 H-107 I-107 J-107 (CH3O)2CHCH2 CH3 C-108 D-108 E-108 F-108 G-108 H-108 I-108 J-108 HOCH2CH2 CH3 C-109 D-109 E-109 F-109 G-109 H-109 I-109 J-109 HOCH2CH2CH2 CH3 C-110 D-110 E-110 F-110 G-110 H-110 I-110 J-110 CH2═CHCH2 PhCH2 C-111 D-111 E-111 F-111 G-111 H-111 I-111 J-111 CHCCH2 PhCH2 C-112 D-112 E-112 F-112 G-112 H-112 I-112 J-112 cyclo-C3H5 PhCH2 C-113 D-113 E-113 F-113 G-113 H-113 I-113 J-113 cyclo-C5H9 PhCH2 C-114 D-114 E-114 F-114 G-114 H-114 I-114 J-114 cyclo-C6H11 PhCH2 C-115 D-115 E-115 F-115 G-115 H-115 I-115 J-115 NH2 PhCH2 C-116 D-116 E-116 F-116 G-116 H-116 I-116 J-116 CH3NH PhCH2 C-117 D-117 E-117 F-117 G-117 H-117 I-117 J-117 C2H5NH PhCH2 C-118 D-118 E-118 F-118 G-118 H-118 I-118 J-118 PhNH PhCH2 C-119 D-119 E-119 F-119 G-119 H-119 I-119 J-119 HO PhCH2 C-120 D-120 E-120 F-120 G-120 H-120 I-120 J-120 CH3O PhCH2 C-121 D-121 E-121 F-121 G-121 H-121 I-121 J-121 C2H5O PhCH2 C-122 D-122 E-122 F-122 G-122 H-122 I-122 J-122 CH2═CHCH2O PhCH2 C-123 D-123 E-123 F-123 G-123 H-123 I-123 J-123 CHCCH2O PhCH2 C-124 D-124 E-124 F-124 G-124 H-124 I-124 J-124 CH3O2CCH2O PhCH2 C-125 D-125 E-125 F-125 G-125 H-125 I-125 J-125 CH3O2CCH(CH3)O PhCH2 C-126 D-126 E-126 F-126 G-126 H-126 I-126 J-126 PhCH2O PhCH2 C-127 D-127 E-127 F-127 G-127 H-127 I-127 J-127 Ph PhCH2 C-128 D-128 E-128 F-128 G-128 H-128 I-128 J-128 4-CF3O—Ph PhCH2 C-129 D-129 E-129 F-129 G-129 H-129 I-129 J-129 4-(4-CF3O)-Ph PhCH2 C-130 D-130 E-130 F-130 G-130 H-130 I-130 J-130 CF3CH2 PhCH2 C-131 D-131 E-131 F-131 G-131 H-131 I-131 J-131 CH3OCH2CH2 PhCH2 C-132 D-132 E-132 F-132 G-132 H-132 I-132 J-132 CH3CH2OCH2CH2 PhCH2 C-133 D-133 E-133 F-133 G-133 H-133 I-133 J-133 CH3OCH2CH2CH2 PhCH2 C-134 D-134 E-134 F-134 G-134 H-134 I-134 J-134 C2H5OCH2CH2CH2 PhCH2 C-135 D-135 E-135 F-135 G-135 H-135 I-135 J-135 n-C4H9OCH2CH2CH2 PhCH2 C-136 D-136 E-136 F-136 G-136 H-136 I-136 J-136 (CH3O)2CHCH2 PhCH2 C-137 D-137 E-137 F-137 G-137 H-137 I-137 J-137 HOCH2CH2 PhCH2 C-138 D-138 E-138 F-138 G-138 H-138 I-138 J-138 HOCH2CH2CH2 PhCH2 C-139 D-139 E-139 F-139 G-139 H-139 I-139 J-139 CH3OCH2CH2CH2 PhCH2 C-140 D-140 E-140 F-140 G-140 H-140 I-140 J-140 C2H5OCH2CH2CH2 PhCH2 C-141 D-141 E-141 F-141 G-141 H-141 I-141 J-141 n-C4H9OCH2CH2CH2 PhCH2 C-142 D-142 E-142 F-142 G-142 H-142 I-142 J-142 (CH3O)2CHCH2 PhCH2 C-143 D-143 E-143 F-143 G-143 H-143 I-143 J-143 HOCH2CH2 PhCH2 C-144 D-144 E-144 F-144 G-144 H-144 I-144 J-144 HOCH2CH2CH2 PhCH2 C-145 D-145 E-145 F-145 G-145 H-145 I-145 J-145 CH2CH2CH2CH2 C-146 D-146 E-146 F-146 G-146 H-146 I-146 J-146 CH2CH2CH2CH2CH2 C-147 D-147 E-147 F-147 G-147 H-147 I-147 J-147 CH2CH2OCH2CH2 C-148 D-148 E-148 F-148 G-148 H-148 I-148 J-148 CH2CH2SCH2CH2 C-149 D-149 E-149 F-149 G-149 H-149 I-149 J-149 CH2CH2NHCH2CH2 C-150 D-150 E-150 F-150 G-150 H-150 I-150 J-150 CH2CH2N(CH3)CH2CH2 C-151 D-151 E-151 F-151 G-151 H-151 I-151 J-151 N═CHCH2CH2

TABLE 3 Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; U is S and m is zero. In Table 3 compounds K-1 to K-151 represent individual compounds in which R² is methyl; compounds L-1 to L-151 represent individual compounds in which R² is ethyl; compounds M-1 to M-151 represent individual compounds in which R² is allyl; compounds N-1 to N-151 represent individual compounds in which R² is propargyl; compounds O-1 to O-151 represent individual compounds in which R² is benzyl; compounds P-1 to P-151 represent individual compounds in which R² is —CH₂CO₂CH₃; compounds Q-1 to Q-151 represent individual compounds in which R² is —CH(CH₃)CO₂CH₃; compounds R-1 to R-151 represent individual compounds in which R² is —CH₂CH(OCH₃)₂. Compound R³ R⁴ K-1 L-1 M-1 N-1 O-1 P-1 Q-1 R-1 CH2═CHCH2 H K-2 L-2 M-2 N-2 O-2 P-2 Q-2 R-2 CH3CH═CHCH2 H K-3 L-3 M-3 N-3 O-3 P-3 Q-3 R-3 CH2═CHCH2CH2 H K-4 L-4 M-4 N-4 O-4 P-4 Q-4 R-4 CHCCH2 H K-5 L-5 M-5 N-5 O-5 P-5 Q-1 R-5 CH3CCCH2 H K-6 L-6 M-6 N-6 O-6 P-6 Q-2 R-6 CHCCH(CH3) H K-7 L-7 M-7 N-7 O-7 P-7 Q-3 R-7 cyclo-C3H5 H K-8 L-8 M-8 N-8 O-8 P-8 Q-4 R-8 cyclo-C5H9 H K-9 L-9 M-9 N-9 O-9 P-9 Q-1 R-9 cyclo-C6H11 H K-10 L-10 M-10 N-10 O-10 P-10 Q-2 R-10 PhCH2 H K-11 L-11 M-11 N-11 O-11 P-11 Q-3 R-11 PhCH(CH3) H K-12 L-12 M-12 N-12 O-12 P-12 Q-4 R-12 NH2 H K-13 L-13 M-13 N-13 O-13 P-13 Q-1 R-13 CH3NH H K-14 L-14 M-14 N-14 O-14 P-14 Q-2 R-14 C2H5NH H K-15 L-15 M-15 N-15 O-15 P-15 Q-3 R-15 n-C3H7NH H K-16 L-16 M-16 N-16 O-16 P-16 Q-4 R-16 iso-C3H7NH H K-17 L-17 M-17 N-17 O-17 P-17 Q-1 R-17 n-C4H9NH H K-18 L-18 M-18 N-18 O-18 P-18 Q-2 R-18 tert-C4H9NH H K-19 L-19 M-19 N-19 O-19 P-19 Q-3 R-19 n-C5H11NH H K-20 L-20 M-20 N-20 O-20 P-20 Q-4 R-20 n-C6H13NH H K-21 L-21 M-21 N-21 O-21 P-21 Q-1 R-21 PhCH2NH H K-22 L-22 M-22 N-22 O-22 P-22 Q-2 R-22 PhNH H K-23 L-23 M-23 N-23 O-23 P-23 Q-3 R-23 HO H K-24 L-24 M-24 N-24 O-24 P-24 Q-4 R-24 CH3O H K-25 L-25 M-25 N-25 O-25 P-25 Q-1 R-25 C2H5O H K-26 L-26 M-26 N-26 O-26 P-26 Q-2 R-26 n-C3H7O H K-27 L-27 M-27 N-27 O-27 P-27 Q-3 R-27 iso-C3H7O H K-28 L-28 M-28 N-28 O-28 P-28 Q-4 R-28 n-C4H9O H K-29 L-29 M-29 N-29 O-29 P-29 Q-1 R-29 tert-C4H9O H K-30 L-30 M-30 N-30 O-30 P-30 Q-2 R-30 CH2═CHCH2O H K-31 L-31 M-31 N-31 O-31 P-31 Q-3 R-31 CHCCH2O H K-32 L-32 M-32 N-32 O-32 P-32 Q-4 R-32 CH3O2CCH2O H K-33 L-33 M-33 N-33 O-33 P-33 Q-1 R-33 CH3O2CCH(CH3)O H K-34 L-34 M-34 N-34 O-34 P-34 Q-2 R-34 CH3O2CC(CH3)2O H K-35 L-35 M-35 N-35 O-35 P-35 Q-3 R-35 PhCH2O H K-36 L-36 M-36 N-36 O-36 P-36 Q-4 R-36 Ph H K-37 L-37 M-37 N-37 O-37 P-37 Q-1 R-37 2-F—Ph H K-38 L-38 M-38 N-38 O-38 P-38 Q-2 R-38 3-F—Ph H K-39 L-39 M-39 N-39 O-39 P-39 Q-3 R-39 4-F—Ph H K-40 L-40 M-40 N-40 O-40 P-40 Q-4 R-40 2-Cl—Ph H K-41 L-41 M-41 N-41 O-41 P-41 Q-1 R-41 3-Cl—Ph H K-42 L-42 M-42 N-42 O-42 P-42 Q-2 R-42 4-Cl—Ph H K-43 L-43 M-43 N-43 O-43 P-43 Q-3 R-43 2-CF3—Ph H K-44 L-44 M-44 N-44 O-44 P-44 Q-4 R-44 3-CF3—Ph H K-45 L-45 M-45 N-45 O-45 P-45 Q-1 R-45 4-CF3—Ph H K-46 L-46 M-46 N-46 O-46 P-46 Q-2 R-46 2-CH3—Ph H K-47 L-47 M-47 N-47 O-47 P-47 Q-3 R-47 3-CH3—Ph H K-48 L-48 M-48 N-48 O-48 P-48 Q-4 R-48 4-CH3—Ph H K-49 L-49 M-49 N-49 O-49 P-49 Q-1 R-49 2-CH3O—Ph H K-50 L-50 M-50 N-50 O-50 P-50 Q-2 R-50 3-CH3O—Ph H K-51 L-51 M-51 N-51 O-51 P-51 Q-3 R-51 4-CH3O—Ph H K-52 L-52 M-52 N-52 O-52 P-52 Q-4 R-52 4-CF3O—Ph H K-53 L-53 M-53 N-53 O-53 P-53 Q-1 R-53 4-CF3CH2O—Ph H K-54 L-54 M-54 N-54 O-54 P-54 Q-2 R-54 4-PhO—Ph H K-55 L-55 M-55 N-55 O-55 P-55 Q-3 R-55 4-(4-Cl—PhO)-Ph H K-56 L-56 M-56 N-56 O-56 P-56 Q-4 R-56 4-(4-CF3—PhO)-Ph H K-57 L-57 M-57 N-57 O-57 P-57 Q-1 R-57 CF3CH2 H K-58 L-58 M-58 N-58 O-58 P-58 Q-2 R-58 ClCH2CH2 H K-59 L-59 M-59 N-59 O-59 P-59 Q-3 R-59 ClCH2CH2CH2 H K-60 L-60 M-60 N-60 O-60 P-60 Q-4 R-60 CH3OCH2CH2 H K-61 L-61 M-61 N-61 O-61 P-61 Q-1 R-61 CH3CH2OCH2CH2 H K-62 L-62 M-62 N-62 O-62 P-62 Q-2 R-62 CH3OCH2CH2CH2 H K-63 L-63 M-63 N-63 O-63 P-63 Q-3 R-63 C2H5OCH2CH2CH2 H K-64 L-64 M-64 N-64 O-64 P-64 Q-4 R-64 n-C4H9OCH2CH2CH2 H K-65 L-65 M-65 N-65 O-65 P-65 Q-1 R-65 CH3OCH(CH3)CH2CH2 H K-66 L-66 M-66 N-66 O-66 P-66 Q-2 R-66 (CH3O)2CHCH2 H K-67 L-67 M-67 N-67 O-67 P-67 Q-3 R-67 HOCH2CH2 H K-68 L-68 M-68 N-68 O-68 P-68 Q-4 R-68 HOCH2CH2CH2 H K-69 L-69 M-69 N-69 O-69 P-69 Q-1 R-69 CH3SCH2CH2 H K-70 L-70 M-70 N-70 O-70 P-70 Q-2 R-70 CH3CH2SCH2CH2 H K-71 L-71 M-71 N-71 O-71 P-71 Q-3 R-71 CH3SCH2CH2CH2 H K-72 L-72 M-72 N-72 O-72 P-72 Q-4 R-72 C2H5SCH2CH2CH2 H K-73 L-73 M-73 N-73 O-73 P-73 Q-1 R-73 CH2═CHCH2 CH3 K-74 L-74 M-74 N-74 O-74 P-74 Q-2 R-74 CHCCH2 CH3 K-75 L-75 M-75 N-75 O-75 P-75 Q-3 R-75 cyclo-C3H5 CH3 K-76 L-76 M-76 N-76 O-76 P-76 Q-4 R-76 cyclo-C5H9 CH3 K-77 L-77 M-77 N-77 O-77 P-77 Q-1 R-77 cyclo-C6H11 CH3 K-78 L-78 M-78 N-78 O-78 P-78 Q-2 R-78 PhCH2 CH3 K-79 L-79 M-79 N-79 O-79 P-79 Q-3 R-79 NH2 CH3 K-80 L-80 M-80 N-80 O-80 P-80 Q-4 R-80 CH3NH CH3 K-81 L-81 M-81 N-81 O-81 P-81 Q-1 R-81 C2H5NH CH3 K-82 L-82 M-82 N-82 O-82 P-82 Q-2 R-82 PhCH2NH CH3 K-83 L-83 M-83 N-83 O-83 P-83 Q-3 R-83 PhNH CH3 K-84 L-84 M-84 N-84 O-84 P-84 Q-4 R-84 HO CH3 K-85 L-85 M-85 N-85 O-85 P-85 Q-1 R-85 CH3O CH3 K-86 L-86 M-86 N-86 O-86 P-86 Q-2 R-86 C2H5O CH3 K-87 L-87 M-87 N-87 O-87 P-87 Q-3 R-87 CH2═CHCH2O CH3 K-88 L-88 M-88 N-88 O-88 P-88 Q-4 R-88 CHCCH2O CH3 K-89 L-89 M-89 N-89 O-89 P-89 Q-1 R-89 CH3O2CCH2O CH3 K-90 L-90 M-90 N-90 O-90 P-90 Q-2 R-90 CH3O2CCH(CH3)O CH3 K-91 L-91 M-91 N-91 O-91 P-91 Q-3 R-91 PhCH2O CH3 K-92 L-92 M-92 N-92 O-92 P-92 Q-4 R-92 Ph CH3 K-93 L-93 M-93 N-93 O-93 P-93 Q-1 R-93 4-CF3O—Ph CH3 K-94 L-94 M-94 N-94 O-94 P-94 Q-2 R-94 4-(4-CF3O)-Ph CH3 K-95 L-95 M-95 N-95 O-95 P-95 Q-3 R-95 CF3CH2 CH3 K-96 L-96 M-96 N-96 O-96 P-96 Q-4 R-96 CH3OCH2CH2 CH3 K-97 L-97 M-97 N-97 O-97 P-97 Q-1 R-97 CH3CH2OCH2CH2 CH3 K-98 L-98 M-98 N-98 O-98 P-98 Q-2 R-98 CH3OCH2CH2CH2 CH3 K-99 L-99 M-99 N-99 O-99 P-99 Q-3 R-99 C2H5OCH2CH2CH2 CH3 K-100 L-100 M-100 N-100 O-100 P-100 Q-4 R-100 n-C4H9OCH2CH2CH2 CH3 K-101 L-101 M-101 N-101 O-101 P-101 Q-1 R-101 (CH3O)2CHCH2 CH3 K-102 L-102 M-102 N-102 O-102 P-102 Q-2 R-102 HOCH2CH2 CH3 K-103 L-103 M-103 N-103 O-103 P-103 Q-3 R-103 HOCH2CH2CH2 CH3 K-104 L-104 M-104 N-104 O-104 P-104 Q-4 R-104 CH3OCH2CH2CH2 CH3 K-105 L-105 M-105 N-105 O-105 P-105 Q-1 R-105 C2H5OCH2CH2CH2 CH3 K-106 L-106 M-106 N-106 O-106 P-106 Q-2 R-106 n-C4H9OCH2CH2CH2 CH3 K-107 L-107 M-107 N-107 O-107 P-107 Q-3 R-107 (CH3O)2CHCH2 CH3 K-108 L-108 M-108 N-108 O-108 P-108 Q-4 R-108 HOCH2CH2 CH3 K-109 L-109 M-109 N-109 O-109 P-109 Q-1 R-109 HOCH2CH2CH2 CH3 K-110 L-110 M-110 N-110 O-110 P-110 Q-2 R-110 CH2═CHCH2 PhCH2 K-111 L-111 M-111 N-111 O-111 P-111 Q-3 R-111 CHCCH2 PhCH2 K-112 L-112 M-112 N-112 O-112 P-112 Q-4 R-112 cyclo-C3H5 PhCH2 K-113 L-113 M-113 N-113 O-113 P-113 Q-1 R-113 cyclo-C5H9 PhCH2 K-114 L-114 M-114 N-114 O-114 P-114 Q-2 R-114 cyclo-C6H11 PhCH2 K-115 L-115 M-115 N-115 O-115 P-115 Q-3 R-115 NH2 PhCH2 K-116 L-116 M-116 N-116 O-116 P-116 Q-4 R-116 CH3NH PhCH2 K-117 L-117 M-117 N-117 O-117 P-117 Q-1 R-117 C2H5NH PhCH2 K-118 L-118 M-118 N-118 O-118 P-118 Q-2 R-118 PhNH PhCH2 K-119 L-119 M-119 N-119 O-119 P-119 Q-3 R-119 HO PhCH2 K-120 L-120 M-120 N-120 O-120 P-120 Q-4 R-120 CH3O PhCH2 K-121 L-121 M-121 N-121 O-121 P-121 Q-1 R-121 C2H5O PhCH2 K-122 L-122 M-122 N-122 O-122 P-122 Q-2 R-122 CH2═CHCH2O PhCH2 K-123 L-123 M-123 N-123 O-123 P-123 Q-3 R-123 CHCCH2O PhCH2 K-124 L-124 M-124 N-124 O-124 P-124 Q-4 R-124 CH3O2CCH2O PhCH2 K-125 L-125 M-125 N-125 O-125 P-125 Q-1 R-125 CH3O2CCH(CH3)O PhCH2 K-126 L-126 M-126 N-126 O-126 P-126 Q-2 R-126 PhCH2O PhCH2 K-127 L-127 M-127 N-127 O-127 P-127 Q-3 R-127 Ph PhCH2 K-128 L-128 M-128 N-128 O-128 P-128 Q-4 R-128 4-CF3O—Ph PhCH2 K-129 L-129 M-129 N-129 O-129 P-129 Q-1 R-129 4-(4-CF3O)-Ph PhCH2 K-130 L-130 M-130 N-130 O-130 P-130 Q-2 R-130 CF3CH2 PhCH2 K-131 L-131 M-131 N-131 O-131 P-131 Q-3 R-131 CH3OCH2CH2 PhCH2 K-132 L-132 M-132 N-132 O-132 P-132 Q-4 R-132 CH3CH2OCH2CH2 PhCH2 K-133 L-133 M-133 N-133 O-133 P-133 Q-1 R-133 CH3OCH2CH2CH2 PhCH2 K-134 L-134 M-134 N-134 O-134 P-134 Q-2 R-134 C2H5OCH2CH2CH2 PhCH2 K-135 L-135 M-135 N-135 O-135 P-135 Q-3 R-135 n-C4H9OCH2CH2CH2 PhCH2 K-136 L-136 M-136 N-136 O-136 P-136 Q-4 R-136 (CH3O)2CHCH2 PhCH2 K-137 L-137 M-137 N-137 O-137 P-137 Q-1 R-137 HOCH2CH2 PhCH2 K-138 L-138 M-138 N-138 O-138 P-138 Q-2 R-138 HOCH2CH2CH2 PhCH2 K-139 L-139 M-139 N-139 O-139 P-139 Q-3 R-139 CH3OCH2CH2CH2 PhCH2 K-140 L-140 M-140 N-140 O-140 P-140 Q-4 R-140 C2H5OCH2CH2CH2 PhCH2 K-141 L-141 M-141 N-141 O-141 P-141 Q-1 R-141 n-C4H9OCH2CH2CH2 PhCH2 K-142 L-142 M-142 N-142 O-142 P-142 Q-2 R-142 (CH3O)2CHCH2 PhCH2 K-143 L-143 M-143 N-143 O-143 P-143 Q-3 R-143 HOCH2CH2 PhCH2 K-144 L-144 M-144 N-144 O-144 P-144 Q-4 R-144 HOCH2CH2CH2 PhCH2 K-145 L-145 M-145 N-145 O-145 P-145 Q-1 R-145 CH2CH2CH2CH2 K-146 L-146 M-146 N-146 O-146 P-146 Q-2 R-146 CH2CH2CH2CH2CH2 K-147 L-147 M-147 N-147 O-147 P-147 Q-3 R-147 CH2CH2OCH2CH2 K-148 L-148 M-148 N-148 O-148 P-148 Q-4 R-148 CH2CH2SCH2CH2 K-149 L-149 M-149 N-149 O-149 P-149 Q-1 R-149 CH2CH2NHCH2CH2 K-150 L-150 M-150 N-150 O-150 P-150 Q-2 R-150 CH2CH2N(CH3)CH2CH2 K-151 L-151 M-151 N-151 O-151 P-151 Q-3 R-151 N═CHCH2CH2

TABLE 4 Compounds of formula (IA): (IA)

Com- pound U R⁷ R⁸ W R⁴ S-1 O H H CH2 H S-2 O H H CH2 n-C3H7 S-3 O H H CH2 iso-C3H7 S-4 O H H CH2 n-C4H9 S-5 O H H CH2 iso-C4H9 S-6 O H H CH2 sec-C4H9 S-7 O H H CH2 tert-C4H9 S-8 O H H CH2 n-C5H11 S-9 O H H CH2 n-C6H13 S-10 O H H CH2 cyclo-C3H5 S-11 O H H CH2 cyclo-C5H9 S-12 O H H CH2 cyclo-C6H11 S-13 O H H CH2 CH2═CHCH2 S-14 O H H CH2 CHCCH2 S-15 O H H CH2 PhCH2 S-16 O H H CH2 Ph(CH3)CH S-17 O H H CH2 Ph(CH3)2C S-18 O H H CH2 Ph S-19 O H H CH2 2-Cl—Ph S-20 O H H CH2 3-Cl—Ph S-21 O H H CH2 4-Cl—Ph S-22 O H H CH2 4-CF3O—Ph S-23 O H H CH2 4-(4-CF3—PhO)—Ph S-24 O CH3 H CH2 C2H5 S-25 O CH3 H CH2 n-C3H7 S-26 O CH3 H CH2 iso-C3H7 S-27 O CH3 H CH2 n-C4H9 S-28 O CH3 H CH2 iso-C4H9 S-29 O CH3 H CH2 sec-C4H9 S-30 O CH3 H CH2 tert-C4H9 S-31 O CH3 H CH2 n-C5H11 S-32 O CH3 H CH2 n-C6H13 S-33 O CH3 H CH2 cyclo-C3H5 S-34 O CH3 H CH2 cyclo-C5H9 S-35 O CH3 H CH2 cyclo-C6H11 S-36 O CH3 H CH2 CH2═CHCH2 S-37 O CH3 H CH2 CHCCH2 S-38 O CH3 H CH2 PhCH2 S-39 O CH3 H CH2 Ph(CH3)CH S-40 O CH3 H CH2 Ph(CH3)2C S-41 O CH3 H CH2 Ph S-42 O CH3 H CH2 2-Cl—Ph S-43 O CH3 H CH2 3-Cl—Ph S-44 O CH3 H CH2 4-Cl—Ph S-45 O CH3 H CH2 4-CF3O—Ph S-46 O CH3 H 0H2 4-(4-CF3—PhO)—Ph S-47 O CH3 CH3 0H2 CH3 S-48 O CH3 CH3 CH2 C2H5 S-49 O CH3 CH3 CH2 n-C3H7 S-50 O CH3 CH3 CH2 iso-C3H7 S-51 O CH3 CH3 CH2 n-C4H9 S-52 O CH3 CH3 CH2 iso-C4H9 S-53 O CH3 CH3 CH2 sec-C4H9 S-54 O CH3 CH3 CH2 tert-C4H9 S-55 O CH3 CH3 CH2 n-C5H11 S-56 O CH3 CH3 CH2 n-C6H13 S-57 O CH3 CH3 CH2 cyclo-C3H5 S-58 O CH3 CH3 CH2 cyclo-C5H9 S-59 O CH3 CH3 CH2 cyclo-C6H11 S-60 O CH3 CH3 CH2 CH2═CHCH2 S-61 O CH3 CH3 CH2 CHCCH2 S-62 O CH3 CH3 CH2 PhCH2 S-63 O CH3 CH3 CH2 Ph(CH3)CH S-64 O CH3 CH3 0H2 Ph(CH3)2C S-65 O CH3 CH3 CH2 Ph S-66 O CH3 CH3 CH2 2-Cl—Ph S-67 O CH3 CH3 CH2 3-Cl—Ph S-68 O CH3 CH3 CH2 4-Cl—Ph S-69 O CH3 CH3 CH2 4-CF3O—Ph S-70 O CH3 CH3 CH2 4-(4-CF3—PhO)—Ph S-71 O OCH3 H CH2 C2H5 S-72 O OCH3 H CH2 n-C3H7 S-73 O OCH3 H CH2 iso-C3H7 S-74 O OCH3 H CH2 n-C4H9 S-75 O OCH3 H CH2 iso-C4H9 S-76 O OCH3 H CH2 sec-C4H9 S-77 O OCH3 H CH2 tert-C4H9 S-78 O OCH3 H CH2 n-C5H11 S-79 O OCH3 H CH2 n-C6H13 S-80 O OCH3 H CH2 cyclo-C3H5 S-81 O OCH3 H CH2 cyclo-C5H9 S-82 O OCH3 H CH2 cyclo-C6H11 S-83 O OCH3 H CH2 CH2═CHCH2 S-84 O OCH3 H CH2 CHCCH2 S-85 O OCH3 H CH2 PhCH2 S-86 O OCH3 H CH2 Ph(CH3)CH S-87 O OCH3 H CH2 Ph(CH3)2C S-88 O OCH3 H CH2 Ph S-89 O OCH3 H CH2 2-Cl—Ph S-90 O OCH3 H CH2 3-Cl—Ph S-91 O OCH3 H CH2 4-Cl—Ph S-92 O OCH3 H CH2 4-CF3O—Ph S-93 O OCH3 H CH2 4-(4-CF3—PhO)—Ph S-94 O OCH2CH3 H CH2 CH3 S-95 O OCH2CH3 H CH2 C2H5 S-96 O OCH2CH3 H CH2 n-C3H7 S-97 O OCH2CH3 H CH2 iso-C3H7 S-98 O OCH2CH3 H CH2 n-C4H9 S-99 O OCH2CH3 H CH2 iso-C4H9 S-100 O OCH2CH3 H CH2 sec-C4H9 S-101 O OCH2CH3 H CH2 tert-C4H9 S-102 O OCH2CH3 H CH2 n-C5H11 S-103 O OCH2CH3 H CH2 n-C6H13 S-104 O OCH2CH3 H CH2 cyclo-C3H5 S-105 O OCH2CH3 H CH2 cyclo-C5H9 S-106 O OCH2CH3 H CH2 cyclo-C6H11 S-107 O OCH2CH3 H CH2 CH2═CHCH2 S-108 O OCH2CH3 H CH2 CHCCH2 S-109 O OCH2CH3 H CH2 PhCH2 S-110 O OCH2CH3 H CH2 Ph(CH3)CH S-111 O OCH2CH3 H CH2 Ph(CH3)2C S-112 O OCH2CH3 H CH2 Ph S-113 O OCH2CH3 H CH2 2-Cl—Ph S-114 O OCH2CH3 H CH2 3-Cl—Ph S-115 O OCH2CH3 H CH2 4-Cl—Ph S-116 O OCH2CH3 H CH2 4-CF3O—Ph S-117 O OCH2CH3 H CH2 4-(4-CF3—PhO)—Ph S-118 O H H C═O H S-119 O H H C═O n-C3H7 S-120 O H H C═O iso-C3H7 S-121 O H H C═O n-C4H9 S-122 O H H C═O iso-C4H9 S-123 O H H C═O sec-C4H9 S-124 O H H C═O tert-C4H9 S-125 O H H C═O n-C5H11 S-126 O H H C═O n-C6H13 S-127 O H H C═O cyclo-C3H5 S-128 O H H C═O cycto-C5H9 S-129 O H H C═O cyclo-C6H11 S-130 O H H C═O CH2═CHCH2 S-131 O H H C═O CHCCH2 S-132 O H H C═O PhCH2 S-133 O H H C═O Ph(CH3)CH S-134 O H H C═O Ph(CH3)20 S-135 O H H C═O Ph S-136 O H H C═O 2-Cl—Ph S-137 O H H C═O 3-Cl—Ph S-138 O H H C═O 4-Cl—Ph S-139 O H H C═O 4-CF3O—Ph S-140 O H H C═O 4-(4-CF3—PhO)—Ph S-141 O CH3 H C═O C2H5 S-142 O CH3 H C═O n-C3H7 S-143 O CH3 H C═O iso-C3H7 S-144 O CH3 H C═O n-C4H9 S-145 O CH3 H C═O iso-C4H9 S-146 O CH3 H C═O sec-C4H9 S-147 O CH3 H C═O tert-C4H9 S-148 O CH3 H C═O n-C5H11 S-149 O CH3 H C═O n-C6H13 S-150 O CH3 H C═O cyclo-C3H5 S-151 O CH3 H C═O cyclo-C5H9 S-152 O CH3 H C═O cyclo-C6H11 S-153 O CH3 H C═O CH2CHCH2 S-154 O CH3 H C═O CHCCH2 S-155 O CH3 H C═O PhCH2 S-156 O CH3 H C═O Ph(CH3)CH S-157 O CH3 H C═O Ph(CH3)2C S-158 O CH3 H C═O Ph S-159 O CH3 H C═O 2-Cl—Ph S-160 O CH3 H C═O 3-Cl—Ph S-161 O CH3 H C═O 4-Cl—Ph S-162 O CH3 H C═O 4-CF3O—Ph S-163 O CH3 H C═O 4-(4-CF3—PhO)—Ph S-164 O CH3 CH3 C═O CH3 S-165 O CH3 CH3 C═O C2H5 S-166 O CH3 CH3 C═O n-C3H7 S-167 O CH3 CH3 C═O iso-C3H7 S-168 O CH3 CH3 C═O n-C4H9 S-169 O CH3 CH3 C═O iso-C4H9 S-170 O CH3 CH3 C═O sec-C4H9 S-171 O CH3 CH3 C═O tert-C4H9 S-172 O CH3 CH3 C═O n-C5H11 S-173 O CH3 CH3 C═O n-C6H13 S-174 O CH3 CH3 C═O cyclo-C3H5 S-175 O CH3 CH3 C═O cyclo-C5H9 S-176 O CH3 CH3 C═O cyclo-C6H11 S-177 O CH3 CH3 C═O CH2═CHCH2 S-178 O CH3 CH3 C═O CHCCH2 S-179 O CH3 CH3 C═O PhCH2 S-180 O CH3 CH3 C═O Ph(CH3)CH S-181 O CH3 CH3 C═O Ph(CH3)20 S-182 O CH3 CH3 C═O Ph S-183 O CH3 CH3 C═O 2-Cl—Ph S-184 O CH3 CH3 C═O 3-Cl—Ph S-185 O CH3 CH3 C═O 4-Cl—Ph S-186 O CH3 CH3 C═O 4-CF3O—Ph S-187 O CH3 CH3 C═O 4-(4-CF3—PhO)—Ph S-188 O OCH3 H C═O C2H5 S-189 O OCH3 H C═O n-C3H7 S-190 O OCH3 H C═O iso-C3H7 S-191 O OCH3 H C═O n-C4H9 S-192 O OCH3 H C═O iso-C4H9 S-193 O OCH3 H C═O sec-C4H9 S-194 O OCH3 H C═O tert-C4H9 S-195 O OCH3 H C═O n-C5H11 S-196 O OCH3 H C═O n-C6H13 S-197 O OCH3 H C═O cyclo-C3H5 S-198 O OCH3 H C═O cyclo-C5H9 S-199 O OCH3 H C═O cyclo-C6H11 S-200 O OCH3 H C═O CH2═CHCH2 S-201 O OCH3 H C═O CHCCH2 S-202 O OCH3 H C═O PhCH2 S-203 O OCH3 H C═O Ph(CH3)CH S-204 O OCH3 H C═O Ph(CH3)2C S-205 O OCH3 H C═O Ph S-206 O OCH3 H C═O 2-Cl—Ph S-207 O OCH3 H C═O 3-Cl—Ph S-208 O OCH3 H C═O 4-Cl—Ph S-209 O OCH3 H C═O 4-CF3O—Ph S-210 O OCH3 H C═O 4-(4-CF3—PhO)—Ph S-211 O OCH2CH3 H C═O CH3 S-212 O OCH2CH3 H C═O C2H5 S-213 O OCH2CH3 H C═O n-C3H7 S-214 O OCH2CH3 H C═O iso-C3H7 S-215 O OCH2CH3 H C═O n-C4H9 S-216 O OCH2CH3 H C═O iso-C4H9 S-217 O OCH2CH3 H C═O sec-C4H9 S-218 O OCH2CH3 H C═O tert-C4H9 S-219 O OCH20H3 H C═O n-C5H11 S-220 O OCH2CH3 H C═O n-C6H13 S-221 O OCH2CH3 H C═O cyclo-C3H5 S-222 O OCH2CH3 H C═O cyclo-C5H9 S-223 O OCH20H3 H C═O cyclo-C6H11 S-224 O OCH2CH3 H C═O CH2═CHCH2 S-225 O OCH2CH3 H C═O CHCCH2 S-226 O OCH2CH3 H C═O PhCH2 S-227 O OCH20H3 H C═O Ph(CH3)CH S-228 O OCH2CH3 H C═O Ph(CH3)2C S-229 O OCH2CH3 H C═O Ph S-230 O OCH2CH3 H C═O 2-Cl—Ph S-231 O OCH2CH3 H C═O 3-Cl—Ph S-232 O OCH2CH3 H C═O 4-Cl—Ph S-233 O OCH2CH3 H C═O 4-CF3O—Ph S-234 O OCH2CH3 H C═O 4-(4-CF3—PhO)—Ph S-235 O H H CH2CH2 C2H5 S-236 O H H CH2CH2 n-C3H7 S-237 O H H CH2CH2 iso-C3H7 S-238 O H H CH2CH2 n-C4H9 S-239 O H H CH2CH2 iso-C4H9 S-240 O H H CH2CH2 sec-C4H9 S-241 O H H CH2CH2 tert-C4H9 S-242 O H H CH2CH2 n-C5H11 S-243 O H H CH2CH2 n-C6H13 S-244 O H H CH2CH2 cyclo-C3H5 S-245 O H H CH2CH2 cyclo-C5H9 S-246 O H H CH2CH2 cyclo-C6H11 S-247 O H H CH2CH2 CH2═CHCH2 S-248 O H H CH2CH2 CHCCH2 S-249 O H H CH2CH2 PhCH2 S-250 O H H CH2CH2 Ph(CH3)CH S-251 O H H CH2CH2 Ph(CH3)2C S-252 O H H CH2CH2 Ph S-253 O H H CH2CH2 2-Cl—Ph S-254 O H H CH2CH2 3-Cl—Ph S-255 O H H CH2CH2 4-Cl—Ph S-256 O H H CH2CH2 4-CF3O—Ph S-257 O H H CH2CH2 4-(4-CF3—PhO)—Ph S-258 O CH3 H CH2CH2 CH3 S-259 O CH3 H CH2CH2 C2H5 S-260 O CH3 H CH2CH2 n-C3H7 S-261 O CH3 H CH2CH2 iso-C3H7 S-262 O CH3 H CH2CH2 n-C4H9 S-263 O CH3 H CH2CH2 iso-C4H9 S-264 O CH3 H CH2CH2 sec-C4H9 S-265 O CH3 H CH2CH2 tert-C4H9 S-266 O CH3 H CH2CH2 n-C5H11 S-267 O CH3 H CH2CH2 n-C6H13 S-268 O CH3 H CH2CH2 cyclo-C3H5 S-269 O CH3 H CH2CH2 cyclo-C5H9 S-270 O CH3 H CH2CH2 cyclo-C6H11 S-271 O CH3 H CH2CH2 CH2═CHCH2 S-272 O CH3 H CH2CH2 CHCCH2 S-273 O CH3 H CH2CH2 PhCH2 S-274 O CH3 H CH2CH2 Ph(CH3)CH S-275 O CH3 H CH2CH2 Ph(CH3)2C S-276 O CH3 H CH2CH2 Ph S-277 O CH3 H CH2CH2 2-Cl—Ph S-278 O CH3 H CH2CH2 3-Cl—Ph S-279 O CH3 H CH2CH2 4-Cl—Ph S-280 O CH3 H CH2CH2 4-CF3O—Ph S-281 O CH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-282 O CH3 CH3 CH2CH2 H S-283 O CH3 CH3 CH2CH2 CH3 S-284 O CH3 CH3 CH2CH2 C2H5 S-285 O CH3 CH3 CH2CH2 n-C3H7 S-286 O CH3 CH3 CH2CH2 iso-C3H7 S-287 O CH3 CH3 CH2CH2 n-C4H9 S-288 O CH3 CH3 CH2CH2 iso-C4H9 S-289 O CH3 CH3 CH2CH2 sec-C4H9 S-290 O CH3 CH3 CH2CH2 tert-C4H9 S-291 O CH3 CH3 CH2CH2 n-C5H11 S-292 O CH3 CH3 CH2CH2 n-C6H13 S-293 O CH3 CH3 CH2CH2 cyclo-C3H5 S-294 O CH3 CH3 CH2CH2 cyclo-C5H9 S-295 O CH3 CH3 CH2CH2 cyclo-C6H11 S-296 O CH3 CH3 CH2CH2 CH2═CHCH2 S-297 O CH3 CH3 CH2CH2 CHCCH2 S-298 O CH3 CH3 CH2CH2 PhCH2 S-299 O CH3 CH3 CH2CH2 Ph(CH3)CH S-300 O CH3 CH3 CH2CH2 Ph(CH3)2C S-301 O CH3 CH3 CH2CH2 Ph S-302 O CH3 CH3 CH2CH2 2-Cl—Ph S-303 O CH3 CH3 CH2CH2 3-Cl—Ph S-304 O CH3 CH3 CH2CH2 4-Cl—Ph S-305 O CH3 CH3 CH2CH2 4-CF3O—Ph S-306 O CH3 CH3 CH2CH2 4-(4-CF3—PhO)—Ph S-307 O OCH3 H CH2CH2 CH3 S-308 O OCH3 H CH2CH2 C2H5 S-309 O OCH3 H CH2CH2 n-C3H7 S-310 O OCH3 H CH2CH2 iso-C3H7 S-311 O OCH3 H CH2CH2 n-C4H9 S-312 O OCH3 H CH2CH2 iso-C4H9 S-313 O OCH3 H CH2CH2 sec-C4H9 S-314 O OCH3 H CH2CH2 tert-C4H9 S-315 O OCH3 H CH2CH2 n-C5H11 S-316 O OCH3 H CH2CH2 n-C6H13 S-317 O OCH3 H CH2CH2 cyclo-C3H5 S-318 O OCH3 H CH2CH2 cyclo-C5H9 S-319 O OCH3 H CH2CH2 cyclo-C6H11 S-320 O OCH3 H CH2CH2 CH2═CHCH2 S-321 O OCH3 H CH2CH2 CHCCH2 S-322 O OCH3 H CH2CH2 PhCH2 S-323 O OCH3 H CH2CH2 Ph(CH3)CH S-324 O OCH3 H CH2CH2 Ph(CH3)2C S-325 O OCH3 H CH2CH2 Ph S-326 O OCH3 H CH2CH2 2-Cl—Ph S-327 O OCH3 H CH2CH2 3-Cl—Ph S-328 O OCH3 H CH2CH2 4-Cl—Ph S-329 O OCH3 H CH2CH2 4-CF3O—Ph S-330 O OCH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-331 O OCH2CH3 H CH2CH2 H S-332 O OCH2CH3 H CH2CH2 CH3 S-333 O OCH2CH3 H CH2CH2 C2H5 S-334 O OCH2CH3 H CH2CH2 n-C3H7 S-335 O OCH2CH3 H CH2CH2 iso-C3H7 S-336 O OCH2CH3 H CH2CH2 n-C4H9 S-337 O OCH2CH3 H CH2CH2 iso-C4H9 S-338 O OCH2CH3 H CH2CH2 sec-C4H9 S-339 O OCH2CH3 H CH2CH2 tert-C4H9 S-340 O OCH2CH3 H CH2CH2 n-C5H11 S-341 O OCH2CH3 H CH2CH2 n-C6H13 S-342 O OCH2CH3 H CH2CH2 cyclo-C3H5 S-343 O OCH2CH3 H CH2CH2 cyclo-C5H9 S-344 O OCH2CH3 H CH2CH2 cyclo-C6H11 S-345 O OCH2CH3 H CH2CH2 CH2═CHCH2 S-346 O OCH2CH3 H CH2CH2 CHCCH2 S-347 O OCH2CH3 H CH2CH2 PhCH2 S-348 O OCH2CH3 H CH2CH2 Ph(CH3)CH S-349 O OCH2CH3 H CH2CH2 Ph(CH3)2C S-350 O OCH2CH3 H CH2CH2 Ph S-351 O OCH2CH3 H CH2CH2 2-Cl—Ph S-352 O OCH2CH3 H CH2CH2 3-Cl—Ph S-353 O OCH2CH3 H CH2CH2 4-Cl—Ph S-354 O OCH2CH3 H CH2CH2 4-CF3O—Ph S-355 O OCH2CH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-356 S H H CH2 H S-357 S H H CH2 n-C3H7 S-358 S H H CH2 iso-C3H7 S-359 S H H CH2 n-C4H9 S-360 S H H CH2 iso-C4H9 S-361 S H H CH2 sec-C4H9 S-362 S H H CH2 tert-C4H9 S-363 S H H CH2 n-C5H11 S-364 S H H CH2 n-C6H13 S-365 S H H CH2 cyclo-C3H5 S-366 S H H CH2 cyclo-C5H9 S-367 S H H CH2 cyclo-C6H11 S-368 S H H CH2 CH2═CHCH2 S-369 S H H CH2 CHCCH2 S-370 S H H CH2 PhCH2 S-371 S H H CH2 Ph(CH3)CH S-372 S H H CH2 Ph(CH3)2C S-373 S H H CH2 Ph S-374 S H H CH2 2-Cl—Ph S-375 S H H CH2 3-Cl—Ph S-376 S H H CH2 4-Cl—Ph S-377 5 H H CH2 4-CF3O—Ph S-378 S H H CH2 4-(4-CF3—PhO)—Ph S-379 S CH3 H CH2 C2H5 S-380 S CH3 H CH2 n-C3H7 S-381 S CH3 H CH2 iso-C3H7 S-382 S CH3 H CH2 n-C4H9 S-383 S CH3 H CH2 iso-C4H9 S-384 S CH3 H CH2 sec-C4H9 S-385 S CH3 H CH2 tert-C4H9 S-386 S CH3 H CH2 n-C5H11 S-387 S CH3 H CH2 n-C6H13 S-388 S CH3 H CH2 cyclo-C3H5 S-389 S CH3 H CH2 cyclo-C5H9 S-390 S CH3 H CH2 cyclo-C6H11 S-391 S CH3 H CH2 CH2═CHCH2 S-392 S CH3 H CH2 CHCCH2 S-393 S CH3 H CH2 PhCH2 S-394 S CH3 H CH2 Ph(CH3)CH S-395 S CH3 H CH2 Ph(CH3)2C S-396 S CH3 H CH2 Ph S-397 S CH3 H CH2 2-Cl—Ph S-398 S CH3 H CH2 3-Cl—Ph S-399 S CH3 H CH2 4-Cl—Ph S-400 S CH3 H CH2 4-CF3O—Ph S-401 5 CH3 H CH2 4-(4-CF3—PhO)—Ph S-402 S CH3 CH3 CH2 CH3 S-403 S CH3 CH3 CH2 C2H5 S-404 S CH3 CH3 CH2 n-C3H7 S-405 S CH3 CH3 CH2 iso-C3H7 S-406 S CH3 CH3 CH2 n-C4H9 S-407 S CH3 CH3 CH2 iso-C4H9 S-408 S CH3 CH3 CH2 sec-C4H9 S-409 S CH3 CH3 CH2 tert-C4H9 S-410 S CH3 CH3 CH2 n-C5H11 S-411 S CH3 CH3 CH2 n-C6H13 S-412 S CH3 CH3 CH2 cyclo-C3H5 S-413 S CH3 CH3 CH2 cyclo-C5H9 S-414 S CH3 CH3 CH2 cyclo-C6H11 S-415 S CH3 CH3 CH2 CH2═CHCH2 S-416 S CH3 CH3 CH2 CHCCH2 S-417 S CH3 CH3 CH2 PhCH2 S-418 S CH3 CH3 CH2 Ph(CH3)CH S-419 S CH3 CH3 CH2 Ph(CH3)2C S-420 S CH3 CH3 CH2 Ph S-421 S CH3 CH3 CH2 2-Cl—Ph S-422 S CH3 CH3 CH2 3-Cl—Ph S-423 S CH3 CH3 CH2 4-Cl—Ph S-424 S CH3 CH3 CH2 4-CF3O—Ph S-425 S CH3 CH3 CH2 4-(4-CF3—PhO)—Ph S-426 S OCH3 H CH2 C2H5 S-427 S OCH3 H CH2 n-C3H7 S-428 S OCH3 H CH2 iso-C3H7 S-429 S OCH3 H CH2 n-C4H9 S-430 S OCH3 H CH2 iso-C4H9 S-431 S OCH3 H CH2 sec-C4H9 S-432 S OCH3 H CH2 tert-C4H9 S-433 S OCH3 H CH2 n-C5H11 S-434 S OCH3 H CH2 n-C6H13 S-435 S OCH3 H CH2 cyclo-C3H5 S-436 S OCH3 H CH2 cyclo-C5H9 S-437 S OCH3 H CH2 cyclo-C6H11 S-438 S OCH3 H CH2 CH2═CHCH2 S-439 S OCH3 H CH2 CHCCH2 S-440 S OCH3 H CH2 PhCH2 S-441 S OCH3 H CH2 Ph(CH3)CH S-442 S OCH3 H CH2 Ph(CH3)2C S-443 S OCH3 H CH2 Ph S-444 S OCH3 H CH2 2-Cl—Ph S-445 S OCH3 H CH2 3-Cl—Ph S-446 S OCH3 H CH2 4-Cl—Ph S-447 S OCH3 H CH2 4-CF3O—Ph S-448 S OCH3 H CH2 4-(4-CF3—PhO)—Ph S-449 S H H CH2CH2 C2H5 S-450 S H H CH2CH2 n-C3H7 S-451 S H H CH2CH2 iso-C3H7 S-452 S H H CH2CH2 n-C4H9 S-453 S H H CH2CH2 iso-C4H9 S-454 S H H CH2CH2 sec-C4H9 S-455 S H H CH2CH2 tert-C4H9 S-456 S H H CH2CH2 n-C5H11 S-457 S H H CH2CH2 n-C6H13 S-458 S H H CH2CH2 cyclo-C3H5 S-459 S H H CH2CH2 cyclo-C5H9 S-460 S H H CH2CH2 cyclo-C6H11 S-461 S H H CH2CH2 CH2═CHCH2 S-462 S H H CH2CH2 CHCCH2 S-463 S H H CH2CH2 PhCH2 S-464 S H H CH2CH2 Ph(CH3)CH S-465 S H H CH2CH2 Ph(CH3)2C S-466 S H H CH2CH2 Ph S-467 S H H CH2CH2 2-Cl—Ph S-468 S H H CH2CH2 3-Cl—Ph S-469 S H H CH2CH2 4-Cl—Ph S-470 S H H CH2CH2 4-CF3O—Ph S-471 S H H CH2CH2 4-(4-CF3—PhO)—Ph S-472 S CH3 H CH2CH2 CH3 S-473 S CH3 H CH2CH2 C2H5 S-474 S CH3 H CH2CH2 n-C3H7 S-475 S CH3 H CH2CH2 iso-C3H7 S-476 S CH3 H CH2CH2 n-C4H9 S-477 S CH3 H CH2CH2 iso-C4H9 S-478 S CH3 H CH2CH2 sec-C4H9 S-479 S CH3 H CH2CH2 tert-C4H9 S-480 S CH3 H CH2CH2 n-C5H11 S-481 S CH3 H CH2CH2 n-C6H13 S-482 S CH3 H CH2CH2 cyclo-C3H5 S-483 S CH3 H CH2CH2 cyclo-C5H9 S-484 S CH3 H CH2CH2 cyclo-C6H11 S-485 S CH3 H CH2CH2 CH2═CHCH2 S-486 S CH3 H CH2CH2 CHCCH2 S-487 S CH3 H CH2CH2 PhCH2 S-488 S CH3 H CH2CH2 Ph(CH3)CH S-489 S CH3 H CH2CH2 Ph(CH3)2C S-490 S CH3 H CH2CH2 Ph S-491 S CH3 H CH2CH2 2-Cl—Ph S-492 S CH3 H CH2CH2 3-Cl—Ph S-493 S CH3 H CH2CH2 4-Cl—Ph S-494 S CH3 H CH2CH2 4-CF3O—Ph S-495 S CH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-496 S CH3 CH3 CH2CH2 H S-497 S CH3 CH3 CH2CH2 CH3 S-498 S CH3 CH3 CH2CH2 C2H5 S-499 S CH3 CH3 CH2CH2 n-C3H7 S-500 S CH3 CH3 CH2CH2 iso-C3H7 S-501 S CH3 CH3 CH2CH2 n-C4H9 S-502 S CH3 CH3 CH2CH2 iso-C4H9 S-503 S CH3 CH3 CH2CH2 sec-C4H9 S-504 S CH3 CH3 CH2CH2 n-C4H9 S-505 S CH3 CH3 CH2CH2 iso-C4H9 S-506 S CH3 CH3 CH2CH2 seo-C4H9 S-507 S CH3 CH3 CH2CH2 tert-C4H9 S-508 S CH3 CH3 CH2CH2 n-C5H11 S-509 S CH3 CH3 CH2CH2 n-C6H13 S-510 S CH3 CH3 CH2CH2 cyclo-C3H5 S-511 S CH3 CH3 CH2CH2 cyclo-C5H9 S-512 S CH3 CH3 CH2CH2 cyclo-C6H11 S-513 S CH3 CH3 CH2CH2 CH2═CHCH2 S-514 S CH3 CH3 CH2CH2 CHCCH2 S-515 S CH3 CH3 CH2CH2 PhCH2 S-516 S CH3 CH3 CH2CH2 Ph(CH3)CH S-517 S CH3 CH3 CH2CH2 Ph(CH3)2C S-518 S CH3 CH3 CH2CH2 Ph S-519 S CH3 CH3 CH2CH2 2-Cl—Ph S-520 S CH3 CH3 CH2CH2 3-Cl—Ph S-521 S CH3 CH3 CH2CH2 4-Cl—Ph S-522 S CH3 CH3 CH2CH2 4-CF3O—Ph S-523 S CH3 CH3 CH2CH2 4-(4-CF3—PhO)—Ph S-524 S OCH3 H CH2CH2 CH3 S-525 S OCH3 H CH2CH2 C2H5 S-526 S OCH3 H CH2CH2 n-C3H7 S-527 S OCH3 H CH2CH2 iso-C3H7 S-528 S OCH3 H CH2CH2 n-C4H9 S-529 S OCH3 H CH2CH2 iso-C4H9 S-530 S OCH3 H CH2CH2 sec-C4H9 S-531 S OCH3 H CH2CH2 tert-C4H9 S-532 S OCH3 H CH2CH2 n-C5H11 S-533 S OCH3 H CH2CH2 n-C6H13 S-534 S OCH3 H CH2CH2 cyclo-C3H5 S-535 S OCH3 H CH2CH2 cyclo-C5H9 S-536 S OCH3 H CH2CH2 cyclo-C6H11 S-537 S OCH3 H CH2CH2 CH2═CHCH2 S-538 S OCH3 H CH2CH2 CHCCH2 S-539 S OCH3 H CH2CH2 PhCH2 S-540 S OCH3 H CH2CH2 Ph(CH3)CH S-541 S OCH3 H CH2CH2 Ph(CH3)2C S-542 S OCH3 H CH2CH2 Ph S-543 S OCH3 H CH2CH2 2-Cl—Ph S-544 S OCH3 H CH2CH2 3-Cl—Ph S-545 S OCH3 H CH2CH2 4-Cl—Ph S-546 S OCH3 H CH2CH2 4-CF3O—Ph S-547 S OCH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-548 O H H CH2 CH3O S-549 O H H CH2 PhCH2O S-550 O H H CH(CH3) H S-551 O H H CH(C2H5) H S-552 O H H CH(C2H5) PhCH2 S-553 O H H CHPh H S-554 O H H CHPh CH3 S-555 O H H CHPh PhCH2 S-556 O CH3 H CH2 H S-557 O Ph H CH2 H S-558 O Ph H CH2 CH3 S-559 O Ph H CH2 PhCH2

TABLE 5 Compounds of formula (IB): (1B)

Compound U X Y R⁴ T-1 O CH CH H T-2 O CH CH n-C3H7 T-3 O CH CH iso-C3H7 T-4 O CH CH n-C4H9 T-5 O CH CH iso-C4H9 T-6 O CH CH sec-C4H9 T-7 O CH CH tert-C4H9 T-8 O CH CH n-C5H11 T-9 O CH CH n-C6H13 T-10 O CH CH cyclo-C3H5 T-11 O CH CH cycfo-C5H9 T-12 O CH CH cyclo-C6H11 T-13 O CH CH CH2═CHCH2 T-14 O CH CH CH2CCH T-15 O CH CH PhCH2 T-16 O CH CH Ph(CH3)OH T-17 O CH CH Ph T-18 O CH CH 2-Cl—Ph T-19 O CH CH 3-Cl—Ph T-20 O CH CH 4-Cl—Ph T-21 O CH CH 4-CF3O—Ph T-22 O CH CH 4-(4-CF3—PhO)—Ph T-23 O CH N H T-24 O CH N CH3 T-25 O CH N n-C4H9 T-26 O CH N iso-C4H9 T-27 O CH N sec-C4H9 T-28 O CH N tert-C4H9 T-29 O CH N n-C5H11 T-30 O CH N n-C6H13 T-31 O CH N cyclo-C3H5 T-32 O CH N cyclo-C5H9 T-33 O CH N cyclo-C6H11 T-34 O CH N CH2═CHCH2 T-35 O CH N CH2CCH T-36 O CH N PhCH2 T-37 O CH N Ph(CH3)CH T-38 O CH N Ph T-39 O CH N 2-Cl—Ph T-40 O CH N 3-Cl—Ph T-41 O CH N 4-Cl—Ph T-42 O CH N 4-CF3O—Ph T-43 O CH N 4-(4-CF3—PhO)—Ph T-44 O CH N H T-45 O N N CH3 T-46 O N N C2H5 T-47 O N N n-C5H11 T-48 O N N n-C6H13 T-49 O N N cyclo-C3H5 T-50 O N N cyclo-C5H9 T-51 O N N cyclo-C6H11 T-52 O N N CH2═CHCH2 T-53 O N N CH2CCH T-54 O N N PhCH2 T-55 O N N Ph(CH3)CH T-56 O N N Ph T-57 O N N 2-Cl—Ph T-58 O N N 3-Cl—Ph T-59 O N N 4-Cl—Ph T-60 O N N 4-CF3O—Ph T-61 O N N 4-(4-CF3—PhO)—Ph T-62 S CH CH H T-63 S CH CH n-C3H7 T-64 S CH CH iso-C3H7 T-65 S CH CH n-C4H9 T-66 S CH CH iso-C4H9 T-67 S CH CH sec-C4H9 T-68 S CH CH tert-C4H9 T-69 S CH CH n-C5H11 T-70 S CH CH n-C6H13 T-71 S CH CH cyclo-C3H5 T-72 S CH CH cyclo-C5H9 T-73 S CH CH cyclo-C6H11 T-74 S CH CH CH2CHCH2 T-75 S CH CH CH2CCH T-76 S CH CH PhCH2 T-77 S CH CH Ph(CH3)CH T-78 S CH CH Ph T-79 S CH CH 2-Cl—Ph T-80 S CH CH 3-Cl—Ph T-81 S CH CH 4-Cl—Ph T-82 S CH CH 4-CF3O—Ph T-83 S CH CH 4-(4-CF3—PhO)—Ph T-84 S CH N H T-85 S CH N CH3 T-86 S CH N n-C4H9 T-87 S CH N iso-C4H9 T-88 S CH N sec-C4H9 T-89 S CH N tert-C4H9 T-90 S CH N n-C5H11 T-91 S CH N n-C6H13 T-92 S CH N cyclo-C3H5 T-93 S CH N cyclo-C5H9 T-94 S CH N cyclo-C6H11 T-95 S CH N CH2═CHCH2 T-96 S CH N CH2CCH T-97 S CH N PhCH2 T-98 S CH N Ph(CH3)OH T-99 S CH N Ph T-100 S CH N 2-Cl—Ph T-101 S CH N 3-Cl—Ph T-102 S CH N 4-Cl—Ph T-103 S CH N 4-CF3O—Ph T-104 S CH N 4-(4-CF3—PhO)—Ph T-105 S N N H T-106 S N N CH3 T-107 S N N C2H5 T-108 S N N n-C5H11 T-109 S N N n-C6H13 T-110 S N N cyclo-C3H5 T-111 S N N cyclo-C5H9 T-112 S N N cyclo-C6H11 T-113 S N N CH2═CHCH2 T-114 S N N CH2CCH T-115 S N N PhCH2 T-116 S N N Ph(CH3)CH T-117 S N N Ph T-118 S N N 2-Cl—Ph T-119 S N N 3-Cl—Ph T-120 S N N 4-Cl—Ph T-121 S N N 4-CF3O—Ph T-122 S N N 4-(4-CF3—PhO)—Ph T-123 S N N Ph

TABLE 6 Compounds of formula (IC): (1C)

Compound U R⁴ R⁹ R¹⁰ U-1 O H H H U-2 O n-C3H7 H H U-3 O iso-C3H7 H H U-4 O n-C4H9 H H U-5 O iso-C4H9 H H U-6 O sec-C4H9 H H U-7 O tert-C4H9 H H U-8 O n-C5H11 H H U-9 O n-C6H13 H H U-10 O cyclo-C3H5 H H U-11 O cyclo-C5H9 H H U-12 O cyclo-C6H11 H H U-13 O CH2CH═CH2 H H U-14 O CH2C(CH3)═CH2 H H U-15 O CH(CH3)CH═CH2 H H U-16 O CH2CH═CHCH3 H H U-17 O CH2CCH H H U-18 O CH2CCCH3 H H U-19 O CH(CH3)CCH H H U-20 O PhCH2 H H U-21 O Ph(CH3)CH H H U-22 O Ph(CH3)2C H H U-23 O Ph H H U-24 O 2-Cl—Ph H H U-25 O 3-Cl—Ph H H U-26 O 4-Cl—Ph H H U-27 S H H H U-28 S n-C3H7 H H U-29 S iso-C3H7 H H U-30 S n-C4H9 H H U-31 S iso-C4H9 H H U-32 S sec-C4H9 H H U-33 S tert-C4H9 H H U-34 S n-C5H11 H H U-35 S n-C6H13 H H U-36 S cyclo-C3H5 H H U-37 S cyclo-C5H9 H H U-38 S cyclo-C6H11 H H U-39 S CH2CH═CH2 H H U-40 S CH2C(CH3)═CH2 H H U-41 S CH(CH3)CH═CH2 H H U-42 S CH2CH═CHCH3 H H U-43 S CH2CCH H H U-44 S CH2CCCH3 H H U-45 S CH(CH3)CCH H H U-46 S PhCH2 H H U-47 S Ph(CH3)CH H H U-48 S Ph(CH3)2C H H U-49 S Ph H H U-50 S 2-Cl—Ph H H U-51 S 3-Cl—Ph H H U-52 S 4-Cl—Ph H H

TABLE 7 Compounds of formula (ID): (1D)

Compound U R⁴ R¹¹ V-1 O H H V-2 O CH3 H V-3 O C2H5 H V-4 O n-C3H7 H V-5 O iso-C3H7 H V-6 O n-C4H9 H V-7 O iso-C4H9 H V-8 O sec-C4H9 H V-9 O tert-C4H9 H V-10 O n-C5H11 H V-11 O n-C6H13 H V-12 O cyclo-C3H5 H V-13 O cyclo-C5H9 H V-14 O cyclo-C6H11 H V-15 O CH2CH═CH2 H V-16 O CH2C(CH3)CH2 H V-17 O CH(CH3)CHCH2 H V-18 O CH2CHCHCH3 H V-19 O CH2CCH H V-20 O CH2CCCH3 H V-21 O CH(CH3)CCH H V-22 O PhCH2 H V-23 O Ph(CH3)CH H V-24 O Ph(CH3)2C H V-25 O Ph H V-26 O 2-Cl—Ph H V-27 O 3-Cl—Ph H V-28 O 4-Cl—Ph H V-29 S H H V-30 S CH3 H V-31 S C2H5 H V-32 S n-C3H7 H V-33 S iso-C3H7 H V-34 S n-C4H9 H V-35 S iso-C4H9 H V-36 S sec-C4H9 H V-37 S tert-C4H9 H V-38 S n-C5H11 H V-39 S n-C6H13 H V-40 S cyclo-C3H5 H V-41 S cyclo-C5H9 H V-42 S cyclo-C6H11 H V-43 S CH2CH═CH2 H V-44 S CH2C(CH3)═CH2 H V-45 S CH(CH3)CH═CH2 H V-46 S CH2CH═CHCH3 H V-47 S CH2CCH H V-48 S CH2CCCH3 H V-49 S CH(CH3)CCH H V-50 S PhCH2 H V-51 S Ph(CH3)CH H V-52 S Ph(CH3)2C H V-53 S Ph H V-54 S 2-Cl—Ph H V-55 S 3-Cl—Ph H V-56 S 4-Cl—Ph H

TABLE 8 Compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, U is NR¹⁸ and m is zero. Compound R³ R⁴ R² R¹⁸ W-1 CH3 H H H W-2 C2H5 H H H W-3 n-C3H7 H H H W-4 iso-C3H7 H H H W-5 n-C4H9 H H H W-6 iso-C4H9 H H H W-7 tert-C4H9 H H H W-8 n-C5H11 H H H W-9 (CH3)3CCH2 H H H W-10 n-C6H13 H H H W-11 CH2═CHCH2 H H H W-12 CHCCH2 H H H W-13 cyclo-C3H5 H H H W-14 cyclo-C5H9 H H H W-15 cyclo-C6H11 H H H W-16 PhCH2 H H H W-17 PhCH(CH3) H H H W-18 CH3NH H H H W-19 C2H5NH H H H W-20 n-C3H7NH H H H W-21 iso-C3H7NH H H H W-22 n-C4H9NH H H H W-23 tert-C4H9NH H H H W-24 n-C5H11NH H H H W-25 n-C6H13NH H H H W-26 PhCH2NH H H H W-27 PhNH H H H W-28 Ph H H H W-29 2-F—Ph H H H W-30 3-F—Ph H H H W-31 4-F—Ph H H H W-32 2-Cl—Ph H H H W-33 3-Cl—Ph H H H W-34 4-Cl—Ph H H H W-35 2-CF3—Ph H H H W-36 3-CF3—Ph H H H W-37 4-CF3—Ph H H H W-38 2-CH3—Ph H H H W-39 3-CH3—Ph H H H W-40 4-CH3—Ph H H H W-41 2-CH3O—Ph H H H W-42 3-CH3O—Ph H H H W-43 4-CH3O—Ph H H H W-44 CF3CH2 H H H W-45 ClCH2CH2 H H H W-46 ClCH2CH2CH2 H H H W-47 CH3OCH2CH2 H H H W-48 CH3CH2OCH2CH2 H H H W-49 CH3OCH2CH2CH2 H H H W-50 C2H5OCH2CH2CH2 H H H W-51 n-C4H9OCH2CH2CH2 H H H W-52 CH3OCH(CH3)CH2CH2 H H H W-53 (CH3O)2CHCH2 H H H W-54 HOCH2CH2 H H H W-55 HOCH2CH2CH2 H H H W-56 CH3SCH2CH2 H H H W-57 CH3CH2SCH2CH2 H H H W-58 CH3SCH2CH2CH2 H H H W-59 C2H5SCH2CH2CH2 H H H W-60 CH2CH2CH2CH2 H H W-61 CH2CH2CH2CH2CH2 H H W-62 CH2CH2OCH2CH2 H H W-63 CH2CH2SCH2CH2 H H W-64 CH2CH2NHCH2CH2 H H W-65 CH2CH2N(CH3)CH2CH2 H H W-66 N═CHCH2CH2 H H W-67 N═CHCH═CH H H W-68 CH3 CH3 H H W-69 C2H5 CH3 H H W-70 n-C3H7 CH3 H H W-71 iso-C3H7 CH3 H H W-72 n-C4H9 CH3 H H W-73 iso-C4H9 CH3 H H W-74 tert-C4H9 CH3 H H W-75 n-C5H11 CH3 H H W-76 n-C6H13 CH3 H H W-77 CH2═CHCH2 CH3 H H W-78 CHCCH2 CH3 H H W-79 cyclo-C3H5 CH3 H H W-80 cyclo-C5H9 CH3 H H W-81 cyclo-C6H11 CH3 H H W-82 PhCH2 CH3 H H W-83 CH3NH CH3 H H W-84 C2H5NH CH3 H H W-85 n-C3H7NH CH3 H H W-86 iso-C3H7NH CH3 H H W-87 n-C4H9NH CH3 H H W-88 tert-C4H9NH CH3 H H W-89 n-C5H11NH CH3 H H W-90 n-C6H13NH CH3 H H W-91 PhCH2NH CH3 H H W-92 PhNH CH3 H H W-93 Ph CH3 H H W-94 2-F—Ph CH3 H H W-95 3-F—Ph CH3 H H W-96 4-F—Ph CH3 H H W-97 2-Cl—Ph CH3 H H W-98 3-Cl—Ph CH3 H H W-99 4-Cl—Ph CH3 H H W-100 2-CF3—Ph CH3 H H W-101 3-CF3—Ph CH3 H H W-102 4-CF3—Ph CH3 H H W-103 2-CH3—Ph CH3 H H W-104 3-CH3—Ph CH3 H H W-105 4-CH3—Ph CH3 H H W-106 2-CH3O—Ph CH3 H H W-107 3-CH3O—Ph CH3 H H W-108 4-CH3O—Ph CH3 H H W-109 CF3CH2 CH3 H H W-110 ClCH2CH2 CH3 H H W-111 ClCH2CH2CH2 CH3 H H W-112 CH3OCH2CH2 CH3 H H W-113 CH3CH2OCH2CH2 CH3 H H W-114 CH3OCH2CH2CH2 CH3 H H W-115 C2H5OCH2CH2CH2 CH3 H H W-116 n-C4H9OCH2CH2CH2 CH3 H H W-117 CH3OCH(CH3)CH2CH2 CH3 H H W-118 (CH3O)2CHCH2 CH3 H H W-119 HOCH2CH2 CH3 H H W-120 HOCH2CH2CH2 CH3 H H W-121 CH3 C2H5 H H W-122 C2H5 C2H5 H H W-123 n-C3H7 C2H5 H H W-124 iso-C3H7 C2H5 H H W-125 CH2═CHCH2 C2H5 H H W-126 CHCCH2 C2H5 H H W-127 cyclo-C3H5 C2H5 H H W-128 PhCH2 C2H5 H H W-129 CH3NH C2H5 H H W-130 C2H5NH C2H5 H H W-131 PhCH2NH C2H5 H H W-132 PhNH C2H5 H H W-133 Ph C2H5 H H W-134 2-Cl—Ph C2H5 H H W-135 3-Cl—Ph C2H5 H H W-136 4-Cl—Ph C2H5 H H W-137 2-CF3—Ph C2H5 H H W-138 3-CF3—Ph C2H5 H H W-139 4-CF3—Ph C2H5 H H W-140 2-CH3O—Ph C2H5 H H W-141 3-CH3O—Ph C2H5 H H W-142 4-CH3O—Ph C2H5 H H W-143 CF3CH2 C2H5 H H W-144 ClCH2CH2 C2H5 H H W-145 ClCH2CH2CH2 C2H5 H H W-146 CH3OCH2CH2 C2H5 H H W-147 CH3CH2OCH2CH2 C2H5 H H W-148 CH3OCH2CH2CH2 C2H5 H H W-149 C2H5OCH2CH2CH2 C2H5 H H W-150 n-C4H9OCH2CH2CH2 C2H5 H H W-151 CH3OCH(CH3)CH2CH2 C2H5 H H W-152 (CH3O)2CHCH2 C2H5 H H W-153 HOCH2CH2 C2H5 H H W-154 HOCH2CH2CH2 C2H5 H H W-155 CH3 H H CH3 W-156 C2H5 H H CH3 W-157 n-C3H7 H H CH3 W-158 iso-C3H7 H H CH3 W-159 tert-C4H9 H H CH3 W-160 CH2═CHCH2 H H CH3 W-161 CHCCH2 H H CH3 W-162 cyclo-C3H5 H H CH3 W-163 PhCH2 H H CH3 W-164 CH3NH H H CH3 W-165 C2H5NH H H CH3 W-166 n-C3H7NH H H CH3 W-167 iso-C3H7NH H H CH3 W-168 PhCH2NH H H CH3 W-169 PhNH H H CH3 W-170 Ph H H CH3 W-171 2-Cl—Ph H H CH3 W-172 3-Cl—Ph H H CH3 W-173 4-Cl—Ph H H CH3 W-174 CH3OCH2CH2 H H CH3 W-175 CH3CH2OCH2CH2 H H CH3 W-176 CH3OCH2CH2CH2 H H CH3 W-177 C2H5OCH2CH2CH2 H H CH3 W-178 n-C4H9OCH2CH2CH2 H H CH3 W-179 CH3OCH(CH3)CH2CH2 H H CH3 W-180 (CH3O)2CHCH2 H H CH3 W-181 HOCH2CH2 H H CH3 W-182 HOCH2CH2CH2 H H CH3 W-183 CH2CH2CH2CH2 H CH3 W-184 CH2CH2CH2CH2CH2 H CH3 W-185 CH2CH2OCH2CH2 H CH3 W-186 CH2CH2SCH2CH2 H CH3 W-187 CH2CH2NHCH2CH2 H CH3 W-188 CH2CH2N(CH3)CH2CH2 H CH3 W-189 N═CHCH2CH2 H CH3 W-190 CH3 H H tert-C4H9 W-191 C2H5 H H tert-C4H9 W-192 n-C3H7 H H tert-C4H9 W-193 iso-C3H7 H H tert-C4H9 W-194 tert-C4H9 H H tert-C4H9 W-195 CH2═CHCH2 H H tert-C4H9 W-196 CHCCH2 H H tert-C4H9 W-197 cyclo-C3H5 H H tert-C4H9 W-198 PhCH2 H H tert-C4H9 W-199 CH3NH H H tert-C4H9 W-200 PhCH2NH H H tert-C4H9 W-201 PhNH H H tert-C4H9 W-202 Ph H H tert-C4H9 W-203 2-Cl—Ph H H tert-C4H9 W-204 3-Cl—Ph H H tert-C4H9 W-205 4-Cl—Ph H H tert-C4H9 W-206 CH3OCH2CH2 H H tert-C4H9 W-207 CH3CH2OCH2CH2 H H tert-C4H9 W-208 CH3OCH2CH2CH2 H H tert-C4H9 W-209 C2H5OCH2CH2CH2 H H tert-C4H9 W-210 (CH3O)2CHCH2 H H tert-C4H9 W-211 HOCH2CH2 H H tert-C4H9 W-212 HOCH2CH2CH2 H H tert-C4H9 W-213 CH2CH2CH2CH2 H tert-C4H9 W-214 CH2CH2CH2CH2CH2 H tert-C4H9 W-215 CH2CH2OCH2CH2 H tert-C4H9 W-216 CH2CH2SCH2CH2 H tert-C4H9 W-217 CH2CH2NHCH2CH2 H tert-C4H9 W-218 CH2CH2N(CH3)CH2CH2 H tert-C4H9 W-219 N═CHCH2CH2 H tert-C4H9 W-220 CH3 H H OH W-221 C2H5 H H OH W-222 n-C3H7 H H OH W-223 iso-C3H7 H H OH W-224 tert-C4H9 H H OH W-225 CH2═CHCH2 H H OH W-226 CHCCH2 H H OH W-227 cyclo-C3H5 H H OH W-228 PhCH2 H H OH W-229 CH3NH H H OH W-230 C2H5NH H H OH W-231 PhCH2NH H H OH W-232 PhNH H H OH W-233 Ph H H OH W-234 2-Cl—Ph H H OH W-235 3-Cl—Ph H H OH W-236 4-Cl—Ph H H OH W-237 CH3OCH2CH2 H H OH W-238 CH3CH2OCH2CH2 H H OH W-239 CH3OCH2CH2CH2 H H OH W-240 C2H5OCH2CH2CH2 H H OH W-241 n-C4H9OCH2CH2CH2 H H OH W-242 CH3OCH(CH3)CH2CH2 H H OH W-243 (CH3O)2CHCH2 H H OH W-244 HOCH2CH2 H H OH W-245 HOCH2CH2CH2 H H OH W-246 CH2CH2CH2CH2 H OH W-247 CH2CH2CH2CH2CH2 H OH W-248 CH2CH2OCH2CH2 H OH W-249 CH2CH2SCH2CH2 H OH W-250 CH2CH2NHCH2CH2 H OH W-251 CH2CH2N(CH3)CH2CH2 H OH W-252 N═CHCH2CH2 H OH W-253 N═CHCH═CH H OH W-254 CH3 H H CH3O W-255 C2H5 H H CH3O W-256 n-C3H7 H H CH3O W-257 iso-C3H7 H H CH3O W-258 tert-C4H9 H H CH3O W-259 CH2═CHCH2 H H CH3O W-260 CHCCH2 H H CH3O W-261 cyclo-C3H5 H H CH3O W-262 PhCH2 H H CH3O W-263 CH3NH H H CH3O W-264 C2H5NH H H CH3O W-265 PhCH2NH H H CH3O W-266 PhNH H H CH3O W-267 Ph H H CH3O W-268 2-Cl—Ph H H CH3O W-269 3-Cl—Ph H H CH3O W-270 4-Cl—Ph H H CH3O W-271 CH3OCH2CH2 H H CH3O W-272 CH3CH2OCH2CH2 H H CH3O W-273 CH3OCH2CH2CH2 H H CH3O W-274 C2H5OCH2CH2CH2 H H CH3O W-275 n-C4H9OCH2CH2CH2 H H CH3O W-276 CH3OCH(CH3)CH2CH2 H H CH3O W-277 (CH3O)2CHCH2 H H CH3O W-278 HOCH2CH2 H H CH3O W-279 HOCH2CH2CH2 H H CH3O W-280 CH3SCH2CH2 H H CH3O W-281 CH3CH2SCH2CH2 H H CH3O W-282 CH3SCH2CH2CH2 H H CH3O W-283 C2H5SCH2CH2CH2 H H CH3O

TABLE 9 Compounds of formula (I) wherein R¹ is —C(═V)OR^(3a) and m is zero. Compound V R^(3a) R² X-1 O cyclo-C3H5 H X-2 O cyclo-C5H9 H X-3 O cyclo-C6H11 H X-4 O CH3NH H X-5 O C2H5NH H X-6 O n-C3H7NH H X-7 O iso-C3H7NH H X-8 O n-C4H9NH H X-9 O tert-C4H9NH H X-10 O n-C5H11NH H X-11 O n-C6H13NH H X-12 O PhCH2NH H X-13 O PhNH H X-14 O CF3CH2 H X-15 O ClCH2CH2 H X-16 O ClCH2CH2CH2 H X-17 O CH3OCH2CH2 H X-18 O CH3CH2OCH2CH2 H X-19 O CH3OCH2CH2CH2 H X-20 O C2H5OCH2CH2CH2 H X-21 O n-C4H9OCH2CH2CH2 H X-22 O CH3OCH(CH3)CH2CH2 H X-23 O (CH3O)2CHCH2 H X-24 O HOCH2CH2 H X-25 O HOCH2CH2CH2 H X-26 O CH3SCH2CH2 H X-27 O CH3CH2SCH2CH2 H X-28 O CH3SCH2CH2CH2 H X-29 O C2H5SCH2CH2CH2 H X-30 O CH3(cyclo-C3H5)CH H X-31 O NCCH2CH2 H X-32 S cyclo-C3H5 H X-33 S cyclo-C5H9 H X-34 S cyclo-C6H11 H X-35 S CH3NH H X-36 S C2H5NH H X-37 S n-C3H7NH H X-38 S iso-C3H7NH H X-39 S n-C4H9NH H X-40 S tert-C4H9NH H X-41 S n-C5H11NH H X-42 S n-C6H13NH H X-43 S PhCH2NH H X-44 S PhNH H X-45 S CF3CH2 H X-46 S ClCH2CH2 H X-47 S ClCH2CH2CH2 H X-48 S CH3OCH2CH2 H X-49 S CH3CH2OCH2CH2 H X-50 S CH3OCH2CH2CH2 H X-51 S C2H5OCH2CH2CH2 H X-52 S n-C4H9OCH2CH2CH2 H X-53 S CH3OCH(CH3)CH2CH2 H X-54 S (CH3O)2CHCH2 H X-55 S HOCH2CH2 H X-56 S HOCH2CH2CH2 H X-57 S CH3SCH2CH2 H X-58 S CH3CH2SCH2CH2 H X-59 S CH3SCH2CH2CH2 H X-60 S C2H5SCH2CH2CH2 H X-61 S CH3(cyclo-C3H5)CH H X-62 S NCCH2CH2 H X-63 O cyclo-C3H5 CH3 X-64 O cyclo-C5H9 CH3 X-65 O cyclo-C6H11 CH3 X-66 O CH3NH CH3 X-67 O C2H5NH CH3 X-68 O n-C3H7NH CH3 X-69 O iso-C3H7NH CH3 X-70 O n-C4H9NH CH3 X-71 O tert-C4H9NH CH3 X-72 O n-C5H11NH CH3 X-73 O n-C6H13NH CH3 X-74 O PhCH2NH CH3 X-75 O PhNH CH3 X-76 O CF3CH2 CH3 X-77 O ClCH2CH2 CH3 X-78 O ClCH2CH2CH2 CH3 X-79 O CH3OCH2CH2 CH3 X-80 O CH3CH2OCH2CH2 CH3 X-81 O CH3OCH2CH2CH2 CH3 X-82 O C2H5OCH2CH2CH2 CH3 X-83 O n-C4H9OCH2CH2CH2 CH3 X-84 O CH3OCH(CH3)CH2CH2 CH3 X-85 O (CH3O)2CHCH2 CH3 X-86 O HOCH2CH2 CH3 X-87 O HOCH2CH2CH2 CH3 X-88 O CH3SCH2CH2 CH3 X-89 O CH3CH2SCH2CH2 CH3 X-90 O CH3SCH2CH2CH2 CH3 X-91 O C2H5SCH2CH2CH2 CH3 X-92 O CH3(cyclo-C3H5)CH CH3 X-93 O NCCH2CH2 CH3 X-94 S cyclo-C3H5 CH3 X-95 S cyclo-C5H9 CH3 X-96 S cyclo-C6H11 CH3 X-97 S CH3NH CH3 X-98 S C2H5NH CH3 X-99 S n-C3H7NH CH3 X-100 S iso-C3H7NH CH3 X-101 S n-C4H9NH CH3 X-102 S tert-C4H9NH CH3 X-103 S n-C5H11NH CH3 X-104 S n-C6H13NH CH3 X-105 S PhCH2NH CH3 X-106 S PhNH CH3 X-107 S CF3CH2 CH3 X-108 S ClCH2CH2 CH3 X-109 S ClCH2CH2CH2 CH3 X-110 S CH3OCH2CH2 CH3 X-111 S CH3CH2OCH2CH2 CH3 X-112 S CH3OCH2CH2CH2 CH3 X-113 S C2H5OCH2CH2CH2 CH3 X-114 S n-C4H9OCH2CH2CH2 CH3 X-115 S CH3OCH(CH3)CH2CH2 CH3 X-116 S (CH3O)2CHCH2 CH3 X-117 S HOCH2CH2 CH3 X-118 S HOCH2CH2CH2 CH3 X-119 S CH3SCH2CH2 CH3 X-120 S CH3CH2SCH2CH2 CH3 X-121 S CH3SCH2CH2CH2 CH3 X-122 S C2H5SCH2CH2CH2 CH3 X-123 S CH3(cyclo-C3H5)CH CH3 X-124 S NCCH2CH2 CH3 X-125 O cyclo-C3H5 C2H5 X-126 O CH3NH C2H5 X-127 O C2H5NH C2H5 X-128 O n-C3H7NH C2H5 X-129 O iso-C3H7NH C2H5 X-130 O n-C4H9NH C2H5 X-131 O tert-C4H9NH C2H5 X-132 O PhCH2NH C2H5 X-133 O PhNH C2H5 X-134 O CF3CH2 C2H5 X-135 O ClCH2CH2 C2H5 X-136 O ClCH2CH2CH2 C2H5 X-137 O CH3OCH2CH2 C2H5 X-138 O CH3CH2OCH2CH2 C2H5 X-139 O CH3OCH2CH2CH2 C2H5 X-140 O C2H5OCH2CH2CH2 C2H5 X-141 O n-C4H9OCH2CH2CH2 C2H5 X-142 O CH3OCH(CH3)CH2CH2 C2H5 X-143 O (CH3O)2CHCH2 C2H5 X-144 O HOCH2CH2 C2H5 X-145 O HOCH2CH2CH2 C2H5 X-146 O CH3(cyclo-C3H5)CH C2H5 X-147 O NCCH2CH2 C2H5 X-148 S cyclo-C3H5 C2H5 X-149 S CH3NH C2H5 X-150 S C2H5NH C2H5 X-151 S n-C3H7NH C2H5 X-152 S iso-C3H7NH C2H5 X-153 S n-C4H9NH C2H5 X-154 S tert-C4H9NH C2H5 X-155 S PhCH2NH C2H5 X-156 S PhNH C2H5 X-157 S CF3CH2 C2H5 X-158 S ClCH2CH2 C2H5 X-159 S ClCH2CH2CH2 C2H5 X-160 S CH3OCH2CH2 C2H5 X-161 S CH3CH2OCH2CH2 C2H5 X-162 S CH3OCH2CH2CH2 C2H5 X-163 S C2H5OCH2CH2CH2 C2H5 X-164 S n-C4H9OCH2CH2CH2 C2H5 X-165 S CH3OCH(CH3)CH2CH2 C2H5 X-166 S (CH3O)2CHCH2 C2H5 X-167 S HOCH2CH2 C2H5 X-168 S HOCH2CH2CH2 C2H5 X-169 S CH3(cyclo-C3H5)CH C2H5 X-170 S NCCH2CH2 C2H5

TABLE 10 1H-NMR spectral details for representative Examples from the above Tables. Nmr spectra were measured in deuterochloroform unless otherwise stated. Cpd 1H-NMR A-2 3.7-3.9(2H, m), 5.1-5.2(2H, m), 5.7-5.9(1H, m), 7.63(1H, d), 8.46(1H, brs), 8.83(1H, d), 8.91(1H, d), 10.70(1H, brs) A-18 2.26(1H, t), 4.02(2H, dd), 7.66(1H, d), 8.34(1H, brs), 8.91(1H, s), 8.94(1H, d), 10.03(1H, brs) A-24 0.5-0.6(1H, m), 0.7-0.8(1H, m), 2.6-2.7(1H, m), 7.65(1H, d), 8.33(1H, brs), 8.89(1H, s), 8.93(1H, d), 9.68(1H, brs) A-26 9.83(1H, s), 8.93(1H, d), 8.89(1H, s), 8.40(1H, d), 7.65(1H, d), 4.12(1H, dt), 2.27(2H, m), 1.98(2H, m), 1.73(2H, m) A-28 1.4-2.0(4H, m), 3.8-4.1(1H, m), 7.64(1H, d), 8.28(1H, brd), 8.90(1H, s), 8.91(1H, d) A-30 1.2-1.4(5H, m), 1.5-1.9(5H, m), 3.4-3.6(1H, m), 7.63(1H, d), 8.22(1H, brd), 8.89(1H, s), 8.91(1H, d) A-32 9.68(1H, s), 8.93(1H, d), 8.90(1H, s), 8.38(1H, t), 7.65(1H, d), 3.10(2H, t), 1.00(1H, m), 0.53(2H, m), 0.22(1H, m) A-37 4.39(2H, d), 7.1-7.4(5H, m), 7.62(1H, d), 8.69(1H, m), 8.7-9.0(3H, m) A-38 1.48(3H, d), 4.7-4.9(1H, m), 7.1-7.4(5H, m), 7.58(1H, d), 8.78(1H, brd), 8.86(1H, s), 8.90(1H, d) A-39 2.80(2H, t), 3.42(2H, t), 7.1-7.4(5H, m), 7.62(1H, d), 8.3-8.5(1H, m), 8.89(1H, s), 8.90(1H, d) A-62 3.80(3H, s), 4.31(1H, s), 6.86(2H, d), 7.16(2H, d), 7.62(1H, d), 8.62(1H, brs), 8.8-9.0(2H, m), 10.26(1H, s) A-64 3.83(3H, s), 7.66(1H, d), 8.89(1H, s), 8.94(1H, d), 9.21(1H, brs), 10.60(1H, brs) A-65 10.54(1H, s), 9.51(1H, s), 8.94(1H, d), 8.89(1H, s), 7.65(1H, d)4.01(2H, q), 1.28(3H, t) A-67 10.39(1H), 8.90-9.05(2H), 7.81(1H), 4.18(1H), 1.24(6H) A-71 1.35(9H, s), 7.62(1H, d), 8.66(1H, s), 8.78(1H, d) A-74 10.58(1H, s), 10.04(1H, s), 8.92(1H, d), 8.89(1H, s), 7.65(1H, d), 5.94(1H, m), 5.38(1H, d), 5.35(1H, d), 4.39(2H, d) A-75 10.51(1H, brs), 8.94(1H, d), 8.89(1H, s), 7.65(1H, d), 5.05(2H, S), 4.34(2H, s), 1.81(3H, s) A-79 10.45(1H, brs), 8.96(1H, d), 8.88(1H, s), 8.52(1H, brs), 7.66(1H, d), 5.85(1H, m), 5.67(1H, m), 4.38(2H, d), 1.77(3H, d) A-81 10.74(1H, brs), 9.37(1H, brs), 8.93(1H, d), 8.89(1H, s), 7.66(1H, d), 4.56(2H, s), 2.60(1H) A-85 1.33(3H, t), 4.29(2H, q), 4.48(2H, s), 7.64(1H, d), 8.85(1H, s), 8.90(1H, d), 9.60(1H, brs), 11.11(1H, brs) A-86 4.92(2H, s), 7.3-7.5(5H, m), 7.63(1H, d), 8.8-9.0(2H, m), 9.91(1H, brs), 10.56(1H, brs) A-88 8.29(1H, d), 8.88(1H, s), 8.86(1H, s), 7.65(1H, d), 7.28(1H, t), 6.93-6.99(3H) 4.93(2H, s), 3.83(3H, s) A-89 8.88(1H, s), 8.76(1H, d), 8.63(1H, s), 7.55(1H, d), 7.36(2H, d), 6.88(2H, d), 4.99(2H, s), 3.79(3H, s) A-90 8.97(1H, d), 8.93(1H, s), 8.52(1H, brs), 7.67(1H, d), 7.35(2H, t), 7.11(2H, d), 7.10(1H, t) A-149 10.32(1H, s), 9.53(1H, s), 8.98-9.01(2H), 7.68(1H, d), 7.44(2H, d), 7.33(2H, t), 7.15(1H, t) A-153 7.0-7.1(1H, m), 7.2-7.3(1H, m), 7.3-7.5(1H, m), 7.68(1H, d), 7.9-8.1(1H, m), 8.9-9.1(2H, m), 9.82(1H, brs), 10.88(1H, brs) A-154 7.0-7.3(3H, m), 7.51(1H, s), 7.71(1H, d), 8.99(1H, s), 9.03(1H, d), 10.21(1H, brs), 10.46(1H, brs) A-155 7.2-7.3(2H, m), 7.4-7.5(2H, m), 7.69(1H, d), 8.94(1H, s), 8.97(1H, d), 10.26(1H, brs), 10.42(1H, brs) A-158 7.3-7.4(2H, m), 7.4-7.5(2H, m), 7.70(1H, d), 8.99(1H, s), 9.02(1H, d), 9.30(1H, brs), 10.33(1H, brs) A-162 7.2-7.3(1H, m), 7.5-7.6(1H, m), 7.6-7.7(2H, m), 7.93(1H, d), 8.96(1H, d), 8.98(1H, s), 9.68(1H, brs), 10.72(1H, brs) A-170 3.82(3H, s), 6.8-6.9(2H, m), 7.3-7.5(2H, m), 7.68(1H, d), 8.9-9.0(2H, m), 9.33(1H, brs), 10.17(1H, brs) A-180 3.99(3H, s), 7.1-7.2(1H, m), 7.4-7.6(1H, m), 7.66(1H, d), 8.0-8.1(1H, m), 8.2-8.3(1H, m), 8.97(1H, d), 9.00(1H, s), 9.39(1H, brs), 12.32(1H, brs) A-190 10.42(1H, s), 9.11(1H, s), 9.01(1H, d), 7.86(1H, d), 7.60(1H, s), 7.53(1H, d), 7.31(1H, t), 7.11(1H, d), 4.62(2H) A-194 7.1-7.3(2H, m), 7.4-7.5(2H, m), 7.69(1H, d), 8.9-9.0(2H, m), 9.65(1H, brs), 10.42(1H, brs) A-200 6.9-7.1(4H, m), 7.3-7.4(2H, m), 7.4-7.5(2H, m), 7.69(1H, d), 8.9-9.0(2H, m), 9.34(1H, brs), 10.30(1H, brs) A-203 10.38(1H, s), 9.58(1H, s), 8.98-9.01(2H), 7.71(1H, d), 7.59(2H, d), 7.49(2H, d), 7.00-7.08(4H) A-204 7.2-7.4(2H, m), 7.70(1H, d), 8.1-8.2(1H, m), 8.79(1H, brs), 8.9-9.1(2H, m), 10.92(1H, brs) A-205 7.0-7.1(1H, m), 7.3-7.4(1H, m), 7.71(1H, d), 7.9-8.0(1H, m), 8.99(1H, s), 9.03(1H, d), 10.08(1H, bes), 11.05(1H, brs) A-206 7.2-7.3(2H, m), 7.3-7.4(2H, m), 7.65(1H, d), 8.92(1H, d), 8.95(1H, s), 9.36(1H, brs), 9.92(1H, brs) A-207 7.1-7.2(1H, m), 7.3-7.4(1H, m), 7.6-7.7(1H, m), 7.72(1H, d), 8.99(1H, s), 9.03(1H, d), 10.21(1H, brs), 10.50(1H, brs) A-208 7.1-7.2(1H, m), 7.4-7.5(2H, m), 7.72(1H, d), 8.97(1H, s), 9.03(1H, d), 9.13(1H, brs), 10.45(1H, brs) A-209 9.07(1H, s), 8.97(1H, d), 8.27(1H, d), 8.00(1H, brs), 7.81(1H, d), 7.74(1H, t), 7.09(1H, t) A-210 10.44(1H, s), 9.33(1H, brs), 9.02(1H, d), 8.99(1H, s), 8.71(1H, S), 8.40(1H, d), 7.98(1H, d), 7.71(1H, d), 7.32(1H, dd) A-211 10.57(1H, s), 9.12(1H, s), 9.02(1H, d), 8.48(2H, d), 7.87(1H, d), 7.63(2H, d) A-212 12.48(1H, brs), 9.63(1H, brs), 8.88(1H, d), 8.81(1H, s), 8.65(2H, d), 7.61(1H, d), 7.07(1H, t) A-222 7.01(1H, d), 7.48(1H, d), 7.71(1H, d), 8.98(1H, s), 9.01(1H, d), 9.92(1H, brs) A-223 7.72(1H, d), 8.33(1H, s), 8.87(1H, s), 8.98(1H, s), 9.01(1H, d), 10.18(1H, brs) A-248 3.8-4.0(2H, m), 7.67(1H, d), 8.6-8.8(1H, m), 8.91(1H, s), 8.96(1H, s), 9.80(1H, brs) A-250 1.9-2.1(2H, m), 3.3-3.5(2H, m), 3.5-3.7(2H, m), 7.65(1H, d), 8.43(1H, brs), 8.90(1H, s), 8.93(1H, d), 10.35(1H, brs) A-251 3.39(3H, s), 3.4-3.6(4H, m), 7.65(1H, d), 8.43(1H, brs), 8.90(1H, s), 8.94(1H, d), 9.02(1H, brs) A-255 0.92(3H, t), 1.3-1.5(2H, m), 1.5-1.7(2H, m), 1.7-1.9(2H, m), 3.2-3.6(6H, m), 7.63(1H, d), 8.45(1H, brs), 8.89(1H, s), 8.91(1H, d), 10.00(1H, brs) A-256 3.3-3.6(m, 8H), 4.44(1H, t), 7.65(1H, d), 8.40(1H, brs), 8.90(1H, s), 8.93(1H, s), 9.40(1H, brs) A-260 3.4-3.5(2H, m), 3.7-3.9(2H, m), 7.67(1H, d), 8.58(1H, brs), 8.91(1H, s), 8.95(1H, d), 9.22(1H, brs) A-261 10.89(1H, s), 8.89-8.93(2H), 8.55(1h, d), 7.66(1H, d), 3.32-3.64(4H), 1.71-1.76(2H) A-262 3.78(3H, s), 3.98(2H, d), 7.64(1H, d), 8.7-8.9(1H, m), 8.89(1H, s), 8.92(1H, d), 10.31(1H, brs) A-265 4.43(2H, d), 7.84(1H, d), 8.81(1H, brs), 9.00(1H, d), 9.08(1H, s) A-267 8.97(1H, d), 8.93(1H, s), 8.60(1H, s), 7.67(1H, d), 1.74(6H, s) A-268 1.0-1.2(6H, m), 1.61(3H, s), 2.1-2.3(1H, m), 7.66(1H, d), 8.73(1H, brs), 8.94(1H, s), 8.96(1H, d), 10.05(1H, brs) A-274 1.5-1.7(4H, m), 2.3-2.6(6H, m), 3.2-3.4(2H, m), 7.62(1H, d), 8.5-8.7(1H, m), 8.8-9.0(2H, m), 10.40(1H, brs) A-292 1.0-1.9(10H, m), 2.88(3H, s), 3.7-4.0(1H, m), 7.55(1H, d), 8.74(1H, s), 8.82(1H, d) A-296 2.98(3H, s), 4.52(2H, s), 7.2-7.4(5H, m), 7.57(1H, d), 8.52(1H, brs), 8.74(1H, s), 8.34(1H, d) A-312 3.11(3H, s), 7.73(1H, d), 8.74(1H, s), 8.87(1H, s), 9.39(1H, s), 9.79(1H, brs) A-313 3.13(3H, s), 3.79(3H, s), 7.57(1H, d), 8.72(1H, s), 8.85(1H, d), 8.90(1H, brs) A-316 1.32(6H, d), 3.12(3H, s), 4.1-4.3(1H, m), 7.56(1H, d), 8.70(1H, s), 8.78(1H, brs), 8.84(1H, d) A-317 3.17(3H, s), 4.40(2H, d), 5.3-5.6(2H, m), 5.9-6.1(1H, m), 7.57(1H, d), 8.68(1H, s), 8.84(1H, d) A-326 1.50(1H, s), 3.09(3H, s), 3.83(3H, s), 5.54(1H, q), 7.58(1H, d), 8.78(1H, s), 8.85(1H, d) A-329 3.13(3H, s), 4.88(2H, s), 7.3-7.5(5H, m), 7.53(1H, d), 8.43(1H, s), 8.59(1H, brs), 8.82(1H, d) A-331 3.17(3H, s), 7.81(1H, d), 8.96(1H, d), 9.13(1H, s), 10.22(1H, brs) A-349 8.84(1H, d), 8.69(1H, s), 7.69(1H, brs), 7.50-7.59(4H), 7.29(2H, d), 3.21(3H, s) A-353 8.84(1H, d), 8.70(1H, s), 7.55-7.62(2H), 7.24-7.46(3H), 3.16(3H, s) A-354 8.84(1H, d), 8.70(1H, s), 7.57(1H, d), 7.45-7.48(2H), 7.32(1H), 7.20(1H), 3.21(3H, s) A-355 8.84(1H, d), 8.69(1H, s), 7.57(1H, s), 7.50(2H, d), 7.24(2H, d), 3.20(3H, s) A-365 8.84(1H, d), 8.67(1H, s), 7.55-7.58(2H), 7.27-7.39(2H), 7.22(1H, d), 3.13(3H, s), 2.30(3H, s) A-366 8.82(1H, d), 8.67(1H, s), 7.77(1H, s), 7.56(1H, d), 7.38(1H, t), 7.23(1H, d)7.06-7.10(2H), 3.18(3H, s), 2.41(3H, s) A-367 8.84(1H, d), 8.68(1H, s), 7.61(1H, s), 7.56(1H, d), 7.30(2H, d), 7.16(2H, d), 3.18(3H, s), 2.42(3H, s) A-369 8.80(1H, d)8.66(1H, s), 7.91(1H, s), 7.55(1H, d), 7.39(1H, t), 6.93(1H, dd), 6.86(1H, d), 6.79(1H, d), 3.83(3H, s), 3.19(3H, s) A-373 8.89(1H, d), 8.85(1H, s), 8.29(2H, d), 7.80(1H, d), 7.73(2H, d), 3.41(3H, s) A-381 8.86(1H, d), 8.73(1H, s), 7.73(1H, d) 7.29(1H, t), 6.83-6.92(3H), 3.19(3H, s) A-398 13.93(1H, s), 8.84(1H, d), 8.75(1H, s), 8.37(1H, d), 7.83(1H, t), 7.58(1H, d), 7.09-7.16(2H), 3.36(3H, s) A-431 3.51(2H, t), 3.64(2H, t), 7.59(1H, d), 8.78(1H, s), 8.82(1H, d), 10.38(1H, brs) A-519 1.11(3H, t), 3.2-3.4(2H, m), 3.4-3.6(2H, m), 3.7-3.9(2H, m), 7.56(1H, d), 8.73(1H, s), 8.80(1H, d) A-524 0.85(3H, t), 1.4-1.7(2H, m), 3.1-3.3(2H, m), 3.4-3.6(2H, m), 3.7-3.9(2H, m), 4.82(1H, brs), 7.56(1H, d), 8.72(1H, s), 8.78(1H, d), 10.54(1H, brs) A-529 8.82(1H, d), 8.62(1H, s), 8.73(1H, brs), 7.54(1H, d), 7.25-7.60(5H), 4.40-4.58(3H), 1.16(6H) A-540 1.16(6H, d), 4.2-4.5(1H, m), 7.63(1H, d), 8.68(1H, s), 8.82(1H, d), 9.02(1H, brs) A-544 8.84(1H, d), 8.69(1H, s), 7.56(1H, d), 4.10-4.25(2H), 1.34(3H, d), 1.21(3H, d) A-564 8.82(1H, d), 8.67(1H, s), 7.50-7.57(3H), 7.15-7.26(3H), 4.65(1H, m), 1.03(6H, d) A-605 1.10(6H, d), 3.3-3.5(2H, m), 3.8-4.0(2H, m), 4.3-4.5(1H, m), 7.54(1H, d), 8.79(1H, s), 8.80(1H, d) A-626 8.88(1H, d), 8.73(1H, s), 7.60(1H, d), 6.41(1H, brs), 1.17(9H, s) A-691 8.82(1H, d), 8.65(1H, s), 7.53(1H, d), 3.95(2H, t), 3.58(2H, t), 1.36(9H, s) A-697 8.82(1H, d), 8.75(1H, brs), 8.71(1H, s), 7.56(1H, s), 5.75(2H, m), 5.19-5.30(4H), 3.29(4H, d) A-713 8.97(1H, s), 8.84(1H, d), 8.73(1H, s), 7.57(1H, d), 5.79(1H, m), 5.26(1H, d), 5.24(1H, d), 4.11(2H, d), 3.78(3H, s) A-736 8.83(1H, d), 8.69(1H, s), 7.45-7.58(5H), 7.24-7.28(2H), 5.78(1H, m), 5.12(1H, d), 5.08(1H, d), 4.17(2H, d), A-737 8.84(1H, d), 8.71(1H, s), 7.55-7.62(2H), 7.27-7.45(3H), 5.80(1H, m), 5.09(1H, d), 5.06(1H, d), 4.49(1H, dd), 3.81(1H, dd) A-738 8.84(1H, d), 8.70(1H, s), 7.57(1H, d), 7.43-7.45(2H), 7.24-7.28(1H9, 7.16(1H, dd), 5.77(1H, m), 5.14(1H, d), 5.10(1H, d), 4.16(2H, d A-744 8.81(1H, d), 8.69(1H, s), 7.68(1H, d), 7.34(1H, t), 6.88-6.95(3H), 5.77(1H, m), 5.05(1H, d), 5.02(1H, d), 4.19(2H, d), 3.80(3H, s) A-745 8.83(1H, d), 8.68(1H, s), 7.56(1H, d), 7.15(2H, d), 6.98(2H, d), 5.76(1H, m), 5.10(1H, d), 5.06(1H, d), 4.12(2H, d), 3.86(3H, s) A-747 8.85(1H, d), 8.70-8.721(2H), 7.72(1H, d), 7.28(1H, t), 6.82-6.89(3H), 5.82(1H, m), 5.03-5.14(2H), 4.20(2H, d) A-748 8.80(!h, d), 8.68(1H, s), 7.84(1H, s), 7.59(1H, d), 7.07(2H, d), 6.89(2H, d), 5.77(1H, m), 5.00-5.30(2H), 4.11(2H, d) A-798 4.61(2H, s), 7.2-7.4(5H, m), 7.54(1H, d), 8.54(1H, s), 8.62(1H, d), 9.18(1H, brs), 10.38(1H, brs) A-799 8.95(1H, s), 8.86(1H, d), 8.73(1H, s), 7.57(1H, d), 7.24-7.36(5H), 4.65(2H, s), 3.68(3H, s) A-805 8.80(1H, d), 8.45(1H, s), 7.53(1H, d), 7.23-7.41(10H), 4.75(2H, s), 4.64(2H, s) A-822 8.86(1H, d), 8.71(1H, s), 7.58(2H), 7.42(3H), 7.24(3H), 7.04-7.11(4H), 4.76(2H, s) A-861 9.30(1H, s), 8.81(1H, d), 8.73(1H, s), 7.55(1H, d), 4.38(1H, m), 3.83(1H, d), 3.03(1H, t), 1.50-1.75(6H), 1.22(3H, d) A-862 3.3-3.5(2H, m), 3.6-3.8(2H, m), 4.47(2H, s), 7.1-7.4(5H, m), 7.57(1H, d), 8.73(1H, s), 8.79(1H, d) A-864 8.79(1H, d), 8.72(1H, s), 7.56(1H, d), 4.45(1H, brs), 3.20-3.80(4H), 1.90-2.10(2H) A-865 8.84(1H, d), 8.74(1H, s), 8.42(1H, brs), 7.57(1H, d), 5.87(2H, brd), 4.33(2H, s), 4.18(2H, s) A-866 11.32(1H, brs), 9.18(1H, s), 9.05(1H, d), 7.97(1H, d), 7.96(1H, d), 7.94(1H, d), 7.47(1H, t), 7.33(1H, t) A-867 8.86(1H, d), 8.78(1H, s), 7.71(1H, d), 7.25-7.45(10H) A-869 3.6-3.9(4H, m), 7.2-7.6(6H, m), 8.67(1H, d), 8.79(1H, m) A-871 1.7-2.2(4H, m), 3.2-3.7(4H, m), 7.56(1H, d), 8.73(1H, s), 8.81(1H, d), 9.11(1H, brs) A-872 1.5-1.8(6H, m), 3.3-3.6(4H, m), 7.56(1H, d), 8.75(1H, s), 8.83(1H, d), 8.93(brs) A-873 3.4-3.6(4H, m), 3.6-3.9(4H, m), 7.58(1H, d), 8.03(1H, brs), 8.76(1H, s), 8.86(1H, d) A-874 2.6-2.8(4H, m), 4.7-4.9(4H, m), 7.59(1H, d), 8.77(1H, s), 8.86(1H, d) B-37 4.85(2H, d), 7.2-7.5(5H, m), 7.62(1H, d), 8.85(1H, s), 8.92(1H, d), 9.74(1H, brs), 10.61(1H, brs) B-40 10.83(1H, s), 8.95(1H, d), 8.91(1H, s), 8.78(1H, s), 7.65(1H, d), 7.25-7.67(5H), 1.91(6H) B-47 10.58(1H), 9.14(1H, s), 8.97(1H, d), 8.90(1H, s), 7.67(1H, d), 7.24-7.38(4H), 4.86(2H, d) B-64 3.84(3H, s), 7.79(1H, s), 8.84(1H, s), 8.93(1H, d), 10.78(1H, brs) B-65 12.41(1H, s), 10.66(1H, s), 8.93(1H, s), 8.87(1H, d), 7.70(1H, d), 4.07(2H, q), 1.16(3H, t) B-71 12.14(1H, s), 9.22(1H, s), 8.98(1H, d), 8.92(1H, s), 7.68(1H, d), 1.43(9H, s) B-74 12.53(1H, s), 10.79(1H, s), 9.00(1H, s), 8.95(1H, d), 7.79(1H, d), 6.02(1H, m), 5.38(1H, d), 5.28(1H, d), 4.60(2H, d) B-86 12.22(1H, s), 9.22(1H, brs), 8.95(1H, d), 8.86(1H, s), 7.66(1H, d), 7.37-7.44(5H), 5.14(2H, s) B-100 2.84(1H, brs), 3.36(1H, brs), 7.87(1H, d), 8.28(1H, brs), 9.03(1H, d), 9.17(1H, s) B-108 5.40(2H, s), 7.2-7.5(5H, m), 7.71(1H, d), 8.9-9.1(2H, m), 12.80(1H, brs) B-109 6.8-7.1(4H, m), 7.3-7.4(1H, m), 7.65(1H, d), 8.90(1H, s), 8.96(1H, d), 8.49(1H, brs), 11.82(1H, d) B-149 12.34(1H, s), 10.95(1H, brs), 9.14(1H, s), 9.02(1H, d), 7.86(1H, d), 7.81(2H, d), 7.44(2H, t), 7.29(1H, m) B-150 12.35(1H, s), 11.15(1H, brs), 9.16(1H, s), 9.03(1H, d), 8.34(1H, t), 7.87(1H, d), 7.25-7.35(3H) B-151 12.45(1H, s), 9.14(1H, s), 9.02(1H, d), 7.49(1H), 7.47(1H, d), 7.46-7.50(2H), 7.07(1H, m) B-152 12.25(1H, s), 11.03(1H, brs), 9.12(1H, s), 9.02(1H, d), 7.86(1H, d), 7.78(2H, t), 7.21(2H, t) B-155 9.09(1H, s), 8.98(1H, d), 7.83(1H, d), 7.78(2H, d), 7.44(2H, d) B-158 9.13(1H, s), 9.02(1H, d), 7.87(1H, d), 7.79(2H, d), 7.62(2H, d) B-163 7.5-7.6(2H, m), 7.67(1H, d), 7.8-7.9(1H, m), 8.01(1H, d), 8.91(1H, s), 8.95(1H, s), 9.82(1H, brs), 12.25(1H, brs) B-166 9.00(1H, s), 8.90(1H, d), 7.74(1H, d), 7.52(1H, d), 7.45(1H, s), 7.19(1H, t), 6.99(1H, d), 2.25(3H, s) B-167 12.29(1H, s), 10.94(1H, brs), 9.13(1H, s), 9.01(1H, d), 7.86(1H, d), 7.66(2H, d), 7.25(2H, d), 2.34(3H, s) B-168 3.97(3H, s), 6.9-7.3(3H, m), 7.88(1H, d), 8.8-8.9(1H, m), 9.03(1H, d), 9.15(1H, s), 10.95(1H, brs), 12.73(1H, brs) B-169 3.83(3H, s), 6.8-6.9(1H, m), 7.2-7.4(2H, m), 7.6-7.7(1H, m), 7.86(1H, d), 9.01(1H, d), 9.13(1H, s), 10.97(1H, brs), 12.38(1H, brs) B-170 3.79(3H, s), 6.95(2H, d), 7.63(2H, d), 7.83(1H, d), 8.98(1H, d), 9.08(1H, s), 10.93(1H, brs), 12.17(1H, brs) B-176 9.14(1H, s), 9.03(1H, d), 8.12(2H, d), 7.88(1H, d), 7.85(2H, d) B-184 12.35(1H, s), 10.96(1H, brs), 9.13(1H, s), 9.02(1H, d), 8.58(1H, s), 7.86(1H, d), 7.53(1H, s), 7.25(1H, t), 7.15(1H, t), 6.76(1H, d) B-185 12.14(1H, s), 10.92(1H, brs), 9.12(1H, s), 9.20(1H, d), 8.54(1H, brs), 7.85(1H, d), 7.56(2H, d), 6.89(2H, d) B-189 4.71(2H, s), 7.2-7.4(2H, m), 7.5-7.6(1H, m), 7.8-7.9(2H, m), 9.01(1H, d), 9.11(1H, s), 11.01(1H, brs), 12.13(1H, brs) B-190 12.38(1H, s), 10.98(1H), 9.15(1H, s), 9.03(1H, d), 7.87(1H, d), 7.74(1H, d), 7.73(1H, s), 7.41(1H, t), 7.30(1H, d), 4.69(3H, s) B-194 12.37(1H, brs), 9.13(1H, s), 9.03(1H, d), 7.92(2H, d), 7.87(1H, d), 7.42(2H, d) B-209 9.99(1H, s), 9.18(1H, s), 9.04(1H, d), 8.48-8.55(3H), 7.88(1H, d) B-247 7.5-8.0(6H, m), 8.99(1H, d), 9.01(1H, s), 10.64(1H, brs) B-251 3.42(3H, s), 3.65(2H, t), 3.8-4.0(2H, m), 7.66(1H, d), 8.89(1H, s), 8.96(1H, d), 9.22(1H, brs), 10.48(1H, brs) B-255 0.91(3H, t), 1.3-1.5(2H, m), 1.5-1.7(2H, m), 1.9-2.1(2H, m), 3.46(3H, t), 3.56(3H, t), 3.81(2H, q), 7.66(1H, d), 8.89(1H, s), 8.97(1H, d), 9.02(1H, brs), 10.53(1H, brs) B-257 1.99(3H, s), 7.88(1H, d), 8.97(1H, d), 8.99(1H, s), 10.92(1H, brs), 12.92(1H, brs) B-258 7.5-7.7(3H, m), 7.86(1H, s), 7.9-8.1(2H, m), 9.02(1H, d), 9.14(1H, brs) B-259 7.3-7.5(5H, m), 7.5-7.7(5H, m), 7.77(1H, d), 8.8-9.0(2H, m), 13.05(1H, brs) B-261 1.8-2.0(2H, m), 3.76(2H, t), 3.8-3.9(2H, m), 7.66(1H, m), 8.99(1H, s), 8.95(1H, d), 9.44(1H, brs), 10.53(1H, brs) B-267 9.08(1H, s), 9.01(1H, d), 7.84(1H, d), 1.95(6H, s) B-269 10.38(1H, brs), 9.35(1H, s), 8.96(1H, d), 8.90(1H, s), 7.67(1H, d), 3.73(4H), 1.60-1.80(4H) B-296 3.23(3H, s), 5.22(2H, s), 7.22-7.5(5H, m), 7.63(1H, d), 8.7-9.0(2H, m) B-313 9.40(1H, s), 8.95(1H, d), 8.75(1H, s), 7.57(1H, d), 3.86(3H, s), 3.58(3H, s) B-331 3.37(3H, s), 4.70(1H, s), 7.53(1H, d), 8.62(1H, s), 8.80(1H, d) B-349 3.69(1H, s), 7.3-7.6(6H, m), 8.33(1H, brs), 8.51(1H, s), 8.79(1h, d) B-353 8.81(1H, d), 8.52(1H, s), 8.52(1H, s), 7.53-7.60(2H), 7.25-7.46(3H), 3.62(3H, s) B-354 10.13(1H), 8.88(1H, d), 8.48(1H, s), 7.72(1H, d), 7.37-7.55(4H), 3.75(3H, s) B-355 8.84(1H, d), 8.57(1H, s), 8.15(1H, s), 7.56(1H, d), 7.43(2H, d), 7.27(2H, d), 3.68(3H, s) B-366 8.81(1H, d), 8.58(1H, s), 8.14(1H, s), 7.54(1H, d), 7.37(1H, d), 7.25(1H), 7.10(2H), 3.65(3H, s), 2.42(3H, s) B-369 8.47(1H, d), 8.03(1H, s), 7.33(1H, d), 7.02(1H, t), 6.54-6.64(3H), 3.45(3H, s), 3.32(3H, s) B-373 8.87(1H, d), 8.62(1H, s), 8.35(1H, s9, 8.31(2H, d), 7.57(1H, d), 7.53(2H, d), 3.78(3H, s) B-398 8.89(1H, d), 8.72(1H, s), 8.51(1H, d), 7.98(1H, dd), 7.73(1H, d), 7.58(1H, d), 7.31(1H, dd), 3.79(3H, s) B-417 9.15(1H, s), 8.88(1H, d), 7.69(1H, d), 4.16(3H, s), 3.56(3H, s) B-431 3.38(3H, s), 3.7-4.2(4H, m), 7.5-7.7(1H, m), 8.7-9.0(2H, m), 10.35(1H, brs) B-519 1.2-1.4(3H, m), 3.7-4.1(6H, m), 7.56(1H, d), 8.6-9.0(2H, m), 10.85(1H, brs) B-564 9.08(1H, brs), 8.36(1H, d), 7.51(1H, brs), 7.23(1H, d), 7.04-7.30(3H), 6.86-6.91(2H), 5.17(1H), 0.74(6H, d) B-713 9.45(1H, s), 8.85(1H, d), 8.76(1H, s), 7.56(1H, d), 5.90(1H, m), 5.27-5.36(2H), 4.70(2H, d), 3.86(3H, s) B-736 8.85(1H, s) 8.27(1H, s), 7.69(1H, d), 7.30-7.50(5H), 6.10(1H, m), 5.28(1H, d), 5.17(1H, d), 4.89(2H, d) B-737 8.83(1H, d), 8.12(1H, s), 7.69(1H, d), 7.54-7.65(2H), 7.38-7.45(2H), 6.05(1H, m), 5.24(1H, d), 5.21(1H, d), 5.00(1H, dd), 4.73(1H, dd) B-738 10.15(1H), 8.86(1H, d), 8.40(1H, s), 7.71(1H, d), 7.35-7.54(4H), 6.00(1H, m), 5.27(1H, d), 5.22(1H, d), 4.93(1H, d) B-744 8.80(1H, d), 8.59(1H, s), 8.11(1H, s), 7.53(1H, d), 7.41(1H, t), 6.96(1H, dd), 6.84(1H, dd), 6.77(1H), 5.94(1H, m), 5.20(1H, d), 5.17(1H, d), 4.73(2H, d), 3.84(3H, s) B-745 8.80(1H, d), 8.67(1H, s), 8.13(1H, s), 7.53(1H, d), 7.17(2H, d), 6.98(2H, d), 5.93(1H, m), 5.17(1H, d), 5.14(1H, d), 4.72(2H, d), 3.85(3H, s) B-747 8.79(1H, d), 8.51(1H, s), 8.34(1H, s), 7.56(1H, d), 7.33(1H, t), 7.26(1H, s), 6.87(1H, dd), 6.79(1H, dd), 6.74(1H, s), 5.91(1H, m), 5.21(1H, d), 5.17(1H, d), 4.73(2H, d) B-748 9.69(1H, s), 8.80(1H, d), 7.96(1H, s), 7.66(1H, d), 7.19(2H, d), 6.86(2H, d), 5.93(1H, m), 5.12-5.25(2H), 4.89(2H, d) B-799 10.45(1H, brs), 8.90(1H, d), 8.86(1H, s), 7.76(1H, d), 7.30-7.46(5H), 5.41(2H, s), 3.88(3H, s) B-805 8.80(1H, d), 8.69(1H, s), 8.45(1H, s), 7.53(1H, d), 7.23-7.41(10H), 4.75(2H, s), 4.64(2H, s) B-822 9.90(1H), 8.84(1H, d), 8.25(1H, s), 7.70(1H, d), 7.24-7.45(10H), 5.62(2H, s) B-861 9.96(1H, brs), 8.95(1H, s), 8.93(1H, d), 7.79(1H, d), 5.40(1H, brs), 4.23(1H, brs), 3.34(1H) 1.60-1.94(6H), 1.33(3H, d) B-863 8.86-8.95(2H), 7.65(1H, d), 5.62(1H), 3.85-4.35(4H), 2.35-2.65(2H) B-864 8.93-8.98(2H), 7.79(1H, d), 4.75(1H), 3.70-4.00(4H), 1.95-2.25(2H) B-865 8.93(2H), 8.42(1H, brs), 7.64(1H, d), 5.9(2H, m), 4.64(2H, s), 4.57(2H, s) B-867 8.81(1H, d), 8.54(1H, s), 8.49(1H, s), 7.54(1H, d), 7.28-7.45(10H) B-868 10.10(1H, s), 8.90(1H, d), 8.82(1H, s), 7.76(1H, d), 7.30-7.53(5H), 2.04(3H, s) B-870 10.38(1H,), 9.37(1H, s), 8.96(1H, d), 8.89(1H, s), 7.67(1H, d), 4.30(2H), 3.74(2H), 3.04(3H, s), 1.85-1.90(4H) B-871 1.9-2.2(4H, m), 3.7-4.0(4H, m), 7.62(1H, d), 8.8-9.0(2H, m) B-872 1.6-1.9(6H, m), 3.6-3.8(2H, m), 4.0-4.3(2H, m), 7.63(2h, d), 8.87(1H, brs), 8.9-9.0(2H, m) B-873 3.5-4.5(6H, m), 7.64(1H, d), 8.56(1H, brs), 8.92(1H, s), 8.94(1H, d) B-874 8.94(1H, d), 8.93(1H, s), 7.65(1H, d), 4.40(2H, brs), 4.02(2H, brs), 2.86(4H) B-877 3.07(2H, dt), 3.96(2H, t), 7.06(1H, s), 7.74(1H, d), 8.73(1H, s), 8.87(1H, d) B-880 1.87(6H, d), 7.2-7.8(6H, m), 8.77(1H, s), 8.83(1H, d) C-10 3.08(3H, s), 4.57(2H, s), 7.2-7.5(5H, m), 7.64(1H, d), 8.72(1H, s), 8.89(1H, d), 9.34(1H, brs) C-78 3.10(3H, s), 3.26(3H, d), 4.5-4.8(2H, m), 7.1-7.5(5H, m), 7.64(1H, d), 8.72(1H, s), 8.90(1H, d), 9.34(1H, brs) C-85 3.02(3H, s), 3.34(3H, s), 3.64(3H, s), 7.58(1H, d), 8.65(1H, d), 8.81(1H, d) C-91 2.88(3H, s), 2.98(3H, s), 4.72(2H, s), 7.30-7.43(5H), 7.59(1H, d), 8.52(1H, s), 8.80(1H, d) D-85 1.33(1H, t), 2.98(3H, s), 3.61(3H, s), 3.87(1H, q), 7.60(1H, d), 8.67(1H, s), 8.82(1H, d) D-86 1.2-1.4(6H, m), 3.7-4.0(4H, m), 7.59(1H, d), 8.67(1H, d), 8.81(1H, d) E-85 2.97(3H, s), 3.59(3H, s), 4.42(2H, d), 5.28(1H, d), 5.32(1H, d), 5.98(1H, m), 7.61(1H, d), 8.68(1H, s), 8.83(1H, d) E-87 3.00(3H, s), 4.25(2H, d), 4.37(2H, d), 5.2-5.5(4H, m), 5.7-6.1(2H, m), 7.61(1H, d), 8.68(1H, s), 8.82(1H, d) F-85 2.35(1H, t), 3.09(3H, s), 3.68(3H, s), 4.64(2H, d), 7.62(1H, d), 8.68(1H, s), 8.85(1H, d) F-88 2.37(1H, dd), 2.62(1H, dd), 3.12(3H, s), 4.50(2H, d), 4.61(2H, d), 7.63(1H, d), 8.73(1H, s), 8.86(1H, d) G-35 4.66(2H, s), 4.75(2H, s), 7.24-7.42(10H), 7.43(1H, d), 8.46(1H, s), 8.83(1H, d) G-85 2.81(3H, s), 3.08(3H, s), 5.06(2H, s), 7.26-7.32(3H), 7.45(2H, d), 7.59(1H, d), 8.70(1H, s), 8.82(1H, d) G-91 2.71(3H, s), 4.29(2H, s), 4.71(2H, s), 7.0-7.1(2H, m), 7.2-7.6(8H, m), 7.58(1H, d), 8.56(1H, s), 8.80(1H, d) G-126 4.31(2H, s), 4.38(2H, s), 4.71(2H, s), 6.89(2H, d), 7.07(2H), 7.17-7.39(11H), 7.50(1H, d), 8.39(1H, s), 8.58(1H, d) H-85 2.96(3H, s), 3.64(3H, s), 3.81(3H, s), 4.59(2H, s), 7.62(1H, d), 8.80(1H, s), 8.85(1H, d) H-89 3.08(3H, S), 3.74(3H, s), 3.77(3H, s), 4.48(2H, s), 4.60(2H, s), 7.64(1H, s), 8.84(1H, s), 8.87(1H, d) H-91 2.90(3H, s), 3.69(3H, s), 4.76(2H, s), 7.24-7.45(5H), 7.64(1H, d), 8.80(1H, s), 8.85(1H, d) I-85 1.60(3H, d), 3.63(3H, s), 3.80(3H, s), 5.30(1H, q), 7.58(1H, d), 8.78(1H, s), 8.84(1H, d) S-2 0.87(3H, t), 1.4-1.7(2H, m), 3.17(2H, t), 3.54(2H, t), 4.06(2H, t), 7.54(1H, d), 8.65(1H, s), 8.81(1H, d) S-3 1.15(6H, d), 3.49(2H, t), 3.9-4.2(3H, m), 7.54(1H, d), 8.66(1H, s), 8.81(1H, d) S-7 1.34(9H, s), 3.58(2H, t), 3.96(2H, t), 7.53(1h, d), 8.65(1h, s), 8.81(1h, d) S-15 3.40(2H, t), 4.01(2H, t), 4.53(2H, s), 7.1-7.4(5H, m), 7.57(1h, d), 8.69(1H, s), 8.83(1H, d) S-18 4.00(2H, t), 4.18(2H, t), 7.1-7.5(5H, m), 7.57(1H, d), 8.70(1H, s), 8.83(1H, d) S-109 1.25(3H, q), 3.1-3.3(1H, d), 3.4-3.6(1H, m), 3.7-4.0(2H, m), 4.28(1H, d), 4.47(1H, d), 5.76(1H, d), 7.1-7.5(5H, m), 7.57(1H, d), 8.70(1H, s), 8.83(1H, d) S-120 1.37(6H, d), 4.2-4.4(1H, m), 4.42(2H, s), 7.62(1H, d), 8.73(1H, s), 8.91(1H, d) S-124 1.55(9H, s), 4.34(2H, s), 7.60(1H, d), 8.71(1H, s), 8.90(1H, d) S-132 4.47(2H, s), 4.62(2H, s), 7.2-7.4(4H, m), 7.61(1H, d), 8.70(1H, s), 8.91(1H, d) S-143 1.36(6H, d), 1.70(3H, d), 4.3-4.4(1H, m), 4.67(1H, q), 7.60(1H, d), 8.71(1H, s), 8.90(1H, d) S-155 1.71(3H, d), 4.76(2H, s), 4.76(1H, q), 7.1-7.4(5H, m), 7.61(1H, d), 8.69(1H, s), 8.91(1H, d) S-167 1.35(6H, d), 1.78(6H, s), 4.2-4.4(1H, m), 7.58(1H, d), 8.67(1H, s), 8.88(1h, d) S-356 3.77(2H, t), 4.40(2H, t), 6.81(1H, brs), 7.54(1H, d), 8.65(1H, s), 8.82(1H, d) S-357 0.94(3H, t), 1.34(1h, m), 1.60(1H, m), 3.63(2H, t), 3.76(2H, t), 4.23(2H, t), 7.51(1H, d), 8.62(1H, s), 8.79(1H, d) S-548 3.69(2H, t), 3.77(3h, s), 4.00(2H, t), 7.57(1H, d), 8.67(1H, s), 8.86(1H, d) S-549 3.43(2H, t), 3.88(2H, t), 4.90(2H, s), 7.30-7.40(5H), 7.57(1H, d), 8.67(1H, s), 8.85(1H, d) S-550 1.40(3H, d), 4.09(1H, m), 4.34(1H, m), 4.64(1H, m), 7.55(1H,, d), 8.78(1H, d), 9.14(1H, s), 9.47(1H, brs) S-551 1.03(3H, t), 1.76(2H, m), 4.19(2H, m), 4.63(1H, m), 7.56(1H, d), 8.80(1H, d), 9.17(1H, s), 9.49(1H, brs) S-552 0.88(3H, t), 1.80(2H, m), 3.82(1H, m), 4.17(1H, d), 4.30(1H, dd), 4.63(1H, t), 5.12(1H, d), 7.23-7.38(5H), 7.53(1H, d), 8.75(1H, d), 9.10(1H, s) S-553 4.38(1H, dd), 4.90(1H, t), 5.27((1H), 7.25-7.53(5H), 7.57(1H, d), 8.81(1H, d), 9.22(1H, s), 9.70(1H, brs) S-554 2.67(3H, s), 3.90(1H, dd), 4.45(1H, dd), 4.65(1h, dd), 7.30(2H), 7.40-7.450(3H), 7.60(1H, d), 8.73(1H, s), 8.87(1H, d) S-555 3.73(1H, d), 4.47(1H, t), 4.66(1H, t), 4.89(1H, t), 5.17(1H, d), 7.10-7.46(10H), 7.57(1H, d), 8.79(1H, d), 9.18(1H, s) S-556 1.56(3H, d), 3.51(1H, dd), 4.02(1h, t), 4.95(1H, m), 7.54(1H, d), 8.78(1H, d), 9.15(1H, s), 9.32(1H, s) S-557 3.90(1H, t), 4.32(1H, t), 5.80(1H, t), 7.38-7.46(5H), 7.57(1H, d), 8.81(1H, d), 9.21(1H, s), 9.42(1H, brs) S-558 3.08(3H, s), 3.60(1H, dd), 4.06(1H, t), 5.78(1H, dd), 7.28-7.40(5H), 7.52(1H, d), 8.74(1H, d), 9.09(1H, s) S-559 3.44(1H, dd), 3.89(1H, t), 4.60(1H, d), 4.73(1H, d), 5.76(1H, dd), 7.26-7.40(10H), 7.53(1H, d9, 8.76(1H, d), 9.13(1H, s) U-3 8.80(1H, d), 8.66(1h, s), 7.54(1H, d), 4.29(2H, t), 4.05(2H, t), 1.18(6H, d) U-7 8.78(1H, d), 8.66(1H, s), 7.52(1H, d), 4.28(2H, t), 4.00(2H, t), 1.34(9H, s) U-20 8.81(1H, d), 8.67(1H, s), 7.55(1H, d), 7.25-7.50(5H), 4.66(2H, s), 4.00-4.17(4H) W-194 1.45(18H, s), 7.54(1H, d), 7.75(1H, d), 9.08(1H, s), 10.17(1H, brs) X-35 3.24(3H, d), 7.67(1H, d), 8.89(1H, s), 8.97(1H, d), 9.24(1H, brs), 10.32(1H, brs) X-43 4.90(2H, d), 7.2-7.5(5H, m), 7.68(1H, d), 8.92(1H, s), 8.98(1H, d), 9.51(1H, brs), 10.62(1H, brs) X-45 9.00(1H, s), 8.97(1H, d), 7.82(1H, d), 5.04(2H, q) X-55 3.77(2H, t), 4.55(2H, t), 7.64(1H, d), 8.84(1H, s), 8.92(1H, d), 9.27(1H, brs)

According to a further feature of the present invention there is provided a method for the control of pests at a locus which comprises the application of an effective amount of a compound of formula (I) or a salt thereof. For this purpose, the said compound is normally used in the form of a pesticidal composition (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in pesticidal compositions), for example as hereinafter described.

The term “compound of the invention” as used hereinafter embraces a 3-pyridylcarboxamide of formula (I) as defined above and a pesticidally acceptable salt thereof.

One aspect of the present invention as defined above is a method for the control of pests at a locus. The locus includes, for example, the pest itself, the place (plant, field, forest, orchard, waterway, soil, plant product, or the like) where the pest resides or feeds, or a place susceptible to future infestation by the pest. The compound of the invention may therefore be applied directly to the pest, to the place where the pest resides or feeds, or to the place susceptible to future infestation by the pest.

As is evident from the foregoing pesticidal uses, the present invention provides pesticidally active compounds and methods of use of said compounds for the control of a number of pest species which includes: arthropods, especially insects or mites, or plant nematodes. The compound of the invention may thus be advantageously employed in practical uses, for example, in agricultural or horticultural crops, in forestry, in veterinary medicine or livestock husbandry, or in public health.

The compounds of the invention may be used for example in the following applications and on the following pests:

For the control of soil insects, such as corn rootworm, termites (especially for protection of structures), root maggots, wireworms, root weevils, stalkborers, cutworms, root aphids, or grubs. They may also be used to provide activity against plant pathogenic nematodes, such as root-knot, cyst, dagger, lesion, or stem or bulb nematodes, or against mites. For the control of soil pests, for example corn rootworm, the compounds are advantageously applied to or incorporated at an effective rate into the soil in which crops are planted or to be planted or to the seeds or growing plant roots.

In the area of public health, the compounds are especially useful in the control of many insects, especially filth flies or other Dipteran pests, such as houseflies, stableflies, soldierflies, hornflies, deerflies, horseflies, midges, punkies, blackflies, or mosquitoes.

In the protection of stored products, for example cereals, including grain or flour, groundnuts, animal feedstuffs, timber or household goods, e.g. carpets and textiles, compounds of the invention are useful against attack by arthropods, more especially beetles, including weevils, moths or mites, for example Ephestia spp. (flour moths), Anthrenus spp. (carpet beetles), Tribolium spp. (flour beetles), Sitophilus spp. (grain weevils) or Acarus spp. (mites).

In the control of cockroaches, ants or termites or similar arthropod pests in infested domestic or industrial premises or in the control of mosquito larvae in waterways, wells, reservoirs or other running or standing water.

For the treatment of foundations, structures or soil in the prevention of the attack on building by termites, for example, Reticulitermes spp., Heterotermes spp., Coptotermes spp.

In agriculture against adults, larvae and eggs of Lepidoptera (butterflies and moths), e.g. Heliothis spp. such as Heliothis virescens (tobacco budworm), Heliothis armigera and Heliothis zea. Against adults and larvae of Coleoptera (beetles) e.g. Anthonomus spp. e.g. grandis (cotton boll weevil), Leptinotarsa decemlineata (Colorado potato beetle), Diabrotica spp. (corn rootworms). Against Heteroptera (Hemiptera and Homoptera) e.g. Psylla spp., Bemisia spp., Trialeurodes spp., Aphis spp., Myzus spp., Megoura viciae, Phylloxera spp., Nephotettix spp. (rice leaf hoppers), Nilaparvata spp.

Against Diptera e.g. Musca spp. Against Thysanoptera such as Thrips tabaci. Against Orthoptera such as Locusta and Schistocerca spp., (locusts and crickets) e.g. Gryllus spp., and Acheta spp. for example, Blatta orientalis, Periplaneta americana, Blatella germanica, Locusta migratoria migratorioides, and Schistocerca gregaria. Against Collembola e.g. Periplaneta spp. and Blatella spp. (roaches). Against arthropods of agricultural significance such as Acari (mites) e.g, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus aselus, Armadium vulgare, Porcellio scaber.

Against nematodes which attack plants or trees of importance to agriculture, forestry or horticulture either directly or by spreading bacterial, viral, mycoplasma or fungal diseases of the plants. The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil-dwelling nematodes such as, for example, those of the genera Meloidogyne (root knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus; Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as Haliocotylenchus multicinctus, Belonoaimus such as Belonoaimus longicaudatus, Longidorus such as Longidorus elongatus, Trichodorus such as Trichodorus primitivus and Xiphinema such as Xiphinema index.

Other nematode genera which can be controlled using the compounds according to the invention are Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (foliar nematodes, such as Aphelenchoides ritzemabosi) and Anguina (seed nematodes, such as Anguina tritici).

In the field of veterinary medicine or livestock husbandry or in the maintenance of public health against arthropods which are parasitic internally or externally upon vertebrates, particularly warm-blooded vertebrates, for example domestic animals, e.g. cattle, sheep, goats, equines, swine, poultry, dogs or cats, for example Acarina, including ticks (e.g. Ixodes spp., Boophilus spp. e.g. Boophilus microplus, Rhipicephalus spp. e.g. Rhipicephalus appendiculatus Ornithodorus spp. (e.g. Ornithodorus moubata) and mites (e.g. Damalinia spp.); fleas; Diptera (e.g. Aedes spp., Anopheles spp., Musca spp., Hypoderma spp.); Hemiptera; Dictyoptera (e.g. Periplaneta spp., Blatella spp.); Hymenoptera; for example against infections of the gastro-intestinal tract caused by parasitic nematode worms, for example members of the family Trichostrongylidae.

From the class of the helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp.

From the class of the Bivalva, for example, Dreissena spp.

In practical use for the control of arthropods, especially insects or acarids, or nematode pests of plants, a method, for example, comprises applying to the plants or to the medium in which they grow an effective amount of a compound of the invention. For such a method, the compound of the invention is generally applied to the locus in which the arthropod or nematode infestation is to be controlled at an effective rate in the range of about 2 g to about 1 kg of the active compound per hectare of locus treated. Under ideal conditions, depending on the pest to be controlled, a lower rate may offer adequate protection. On the other hand, adverse weather conditions, resistance of the pest or other factors may require that the active ingredient be used at higher rates. The optimum rate depends usually upon a number of factors, for example, the type of pest being controlled, the type or the growth stage of the infested plant, the row spacing or also the method of application. Preferably an effective rate range of the active compound is from about 10 g/ha to about 400 g/ha, more preferably from about 50 g/ha to about 200 g/ha.

When a pest is soil-borne, the active compound generally in a formulated composition, is distributed evenly over the area to be treated (ie, for example broadcast or band treatment) in any convenient manner and is applied at rates from about 10 g/ha to about 400 g ai/ha, preferably from about 50 g/ha to about 200 g ai/ha. When applied as a root dip to seedlings or drip irrigation to plants the liquid solution or suspension contains from about 0.075 to about 1000 mg ai/l, preferably from about 25 to about 200 mg ai/l. Application may be made, if desired, to the field or crop-growing area generally or in close proximity to the seed or plant to be protected from attack. The compound of the invention can be washed into the soil by spraying with water over the area or can be left to the natural action of rainfall. During or after application, the formulated compound can, if desired, be distributed mechanically in the soil, for example by ploughing, disking, or use of drag chains. Application can be prior to planting, at planting, after planting but before sprouting has taken place, or after sprouting.

The compound of the invention and methods of control of pests therewith are of particular value in the protection of field, forage, plantation, glasshouse, orchard or vineyard crops, of ornamentals, or of plantation or forest trees, for example: cereals (such as wheat or rice), cotton, vegetables (such as peppers), field crops (such as sugar beets, soybeans or oil seed rape), grassland or forage crops (such as maize or sorghum), orchards or groves (such as of stone or pit fruit or citrus), ornamental plants, flowers or vegetables or shrubs under glass or in gardens or parks, or forest trees (both deciduous and evergreen) in forests, plantations or nurseries.

They are also valuable in the protection of timber (standing, felled, converted, stored or structural) from attack, for example, by sawflies or beetles or termites.

They have applications in the protection of stored products such as grains, fruits, nuts, spices or tobacco, whether whole, milled or compounded into products, from moth, beetle, mite or grain weevil attack. Also protected are stored animal products such as skins, hair, wool or feathers in natural or converted form (e.g. as carpets or textiles) from moth or beetle attack as well as stored meat, fish or grains from beetle, mite or fly attack.

Additionally, the compound of the invention and methods of use thereof are of particular value in the control of arthropods or helminths which are injurious to, or spread or act as vectors of diseases domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges, or biting, nuisance or myiasis flies. The compounds of the invention are particularly useful in controlling arthropods or helminths which are present inside domestic host animals or which feed in or on the skin or suck the blood of the animal, for which purpose they may be administered orally, parenterally, percutaneously or topically.

The compositions hereinafter described for application to growing crops or crop growing loci or as a seed dressing may, in general, alternatively be employed in the protection of stored products, household goods, property or areas of the general environment. Suitable means of applying the compounds of the invention include: to growing crops as foliar sprays (for example as an in-furrow spray), dusts, granules, fogs or foams or also as suspensions of finely divided or encapsulated compositions as soil or root treatments by liquid drenches, dusts, granules, smokes or foams; to seeds of crops via application as seed dressings by liquid slurries or dusts;

to animals infested by or exposed to infestation by arthropods or helminths, by parenteral, oral or topical application of compositions in which the active ingredient exhibits an immediate and/or prolonged action over a period of time against the arthropods or helminths, for example by incorporation in feed or suitable orally-ingestible pharmaceutical formulations, edible baits, salt licks, dietary supplements, pour-on formulations, sprays, baths, dips, showers, jets, dusts, greases, shampoos, creams, wax smears or livestock self-treatment systems;

to the environment in general or to specific locations where pests may lurk, including stored products, timber, household goods, or domestic or industrial premises, as sprays, fogs, dusts, smokes, wax-smears, lacquers, granules or baits, or in tricklefeeds to waterways, wells, reservoirs or other running or standing water.

The compounds of the formula (I) can also be employed for controlling harmful organisms in crops of known genetically engineered plants or genetically engineered plants yet to be developed. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to particular crop protection agents, resistances to plant diseases or pathogens of plant diseases, such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties concern, for example, the harvested material with regard to quantity, quality, storage properties, composition and specific constituents. Thus, transgenic plants are known where the starch content is increased, or the starch quality is altered, or where the harvested material has a different fatty acid composition.

The use in economically important transgenic crops of useful plants and ornamentals is preferred, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other types of vegetables.

When used in transgenic crops, in particular those which have resistances to insects, effects are frequently observed, in addition to the effects against harmful organisms to be observed in other crops, which are specific for application in the transgenic crop in question, for example an altered or specifically widened spectrum of pests which can be controlled, or altered application rates which may be employed for application.

The invention therefore also relates to the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.

According to a further feature of the present invention there is provided a pesticidal composition comprising one or more compounds of the invention as defined above, in association with, and preferably homogeneously dispersed in one or more compatible pesticidally acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in pesticidal compositions and which are compatible with compounds of the invention].

In practice, the compounds of the invention most frequently form parts of compositions. These compositions can be employed to control arthropods, especially insects and acarids, or helminths such as plant nematodes. The compositions may be of any type known in the art suitable for application to the desired pest in any premises or indoor or outdoor area. These compositions contain at least one compound of the invention as the active ingredient in combination or association with one or more other compatible components which are for example, solid or liquid carriers or diluents, adjuvants, surface-active-agents, or the like appropriate for the intended use and which are agronomically or medicinally acceptable. These compositions, which may be prepared by any manner known in the art, likewise form a part of this invention.

The compounds of the invention, in their commercially available formulations and in the use forms prepared from these formulations may be present in mixtures with other active substances such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulatory substances or herbicides.

The pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, formamidines, tin compounds and materials produced by microorganisms. Preferred components in mixtures are:

1. from the group of the phosphorus compounds

acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of the carbamates

alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

3. from the group of the carboxylic esters

acrinathrin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentylisomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl(1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, phenothrin (® isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin, tralomethrin, transfluthrin, zeta-cypermethrin (F-56701);

4. from the group of the amidines

amitraz, chlordimeform;

5. from the group of the tin compounds

cyhexatin, fenbutatin oxide;

6. others

abamectin, ABG-9008, acetamiprid, acequinocyl, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, azadirachtin, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate, binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, chlorproxyfen, chromafenozide, clothianidine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, DBI-3204, ethyl 2-chloro-N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-carboximidate, DDT, d icofol, diflubenzu ron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, diofenolan, emamectin benzoate, endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, fluacrypyrim, flubenzimine, flubrocythrinate, flucycloxuron, flufenoxuron, flufenzine, flufenprox, fluproxyfen, gamma-HCH, halfenozide, halofenprox, hexaflumuron (DE_(—)473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI-220, indoxacarb, ivermectin, L-14165, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), lufenuron, M-020, M-020, methoxyfenozide, milbemectin, NC-196, neemgard, nidinoterfuran, nitenpyram, 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), novaluron, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, pyriproxyfen, NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, OK-9802, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine (CG-177), spinosad, spirodiclofen, SU-9118, tebufenozide, tebufenpyrad, teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn A, triflumuron, verbutin, vertalec (mykotal), YI-5301.

The abovementioned components for combinations are known active substances, many of which are described in Ch. R Worthing, S. B. Walker, The Pesticide Manual, 12^(th) Edition, British Crop Protection Council, Farnham 2000.

The effective use doses of the compounds employed in the invention can vary within wide limits, particularly depending on the nature of the pest to be eliminated or degree of infestation, for example, of crops with these pests. In general, the compositions according to the invention usually contain about 0.05 to about 95% (by weight) of one or more active ingredients according to the invention, about 1 to about 95% of one or more solid or liquid carriers and, optionally, about 0.1 to about 50% of one or more other compatible components, such as surface-active agents or the like. In the present account, the term “carrier” denotes an organic or inorganic ingredient, natural or synthetic, with which the active ingredient is combined to facilitate its application, for example, to the plant, to seeds or to the soil. This carrier is therefore generally inert and it must be acceptable (for example, agronomically acceptable, particularly to the treated plant).

The carrier may be a solid, for example, clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (for example ammonium salts), ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earth, or ground synthetic minerals, such as silica, alumina, or silicates especially aluminium or magnesium silicates. As solid carriers for granules the following are suitable: crushed or fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite; synthetic granules of inorganic or organic meals; granules of organic material such as sawdust, coconut shells, corn cobs, corn husks or tobacco stalks; kieselguhr, tricalcium phosphate, powdered cork, or absorbent carbon black; water soluble polymers, resins, waxes; or solid fertilizers. Such solid compositions may, if desired, contain one or more compatible wetting, dispersing, emulsifying or colouring agents which, when solid, may also serve as a diluent.

The carrier may also be liquid, for example: water; alcohols, particularly butanol or glycol, as well as their ethers or esters, particularly methylglycol acetate; ketones, particularly acetone, cyclohexanone, methylethyl ketone, methylisobutylketone, or isophorone; petroleum fractions such as paraffinic or aromatic hydrocarbons, particularly xylenes or alkyl naphthalenes; mineral or vegetable oils; aliphatic chlorinated hydrocarbons, particularly trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, particularly chlorobenzenes; water-soluble or strongly polar solvents such as dimethylformamide, dimethyl sulphoxide, or N-methylpyrrolidone; liquefied gases; or the like or a mixture thereof.

The surface-active agent may be an emulsifying agent, dispersing agent or wetting agent of the ionic or non-ionic type or a mixture of such surface-active agents. Amongst these are e.g., salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (particularly alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (particularly alkyltaurates), phosphoric esters of alcohols or of polycondensates of ethylene oxide with phenols, esters of fatty acids with polyols, or sulphate, sulphonate or phosphate functional derivatives of the above compounds. The presence of at least one surface-active agent is generally essential when the active ingredient and/or the inert carrier are only slightly water soluble or are not water soluble and the carrier agent of the composition for application is water. Compositions of the invention may further contain other additives such as adhesives or colorants. Adhesives such as carboxymethylcellulose or natural or synthetic polymers in the form of powders, granules or lattices, such as arabic gum, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as cephalins or lecithins, or synthetic phospholipids can be used in the formulations. It is possible to use colorants such as inorganic pigments, for example: iron oxides, titanium oxides or Prussian Blue; organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs; or trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.

For their agricultural application, the compounds of the invention are therefore generally in the form of compositions, which are in various solid or liquid forms. Solid forms of compositions which can be used are dusting powders (with a content of the compound of the invention, ranging up to 80%), wettable powders or granules (including water dispersible granules), particularly those obtained by extrusion, compacting, impregnation of a granular carrier, or granulation starting from a powder (the content of the compound of the invention, in these wettable powders or granules being between about 0.5 and about 80%). Solid homogenous or heterogenous compositions containing one or more compounds of the invention, for example granules, pellets, briquettes or capsules, may be used to treat standing or running water over a period of time. A similar effect may be achieved using trickle or intermittent feeds of water dispersible concentrates as described herein.

Liquid compositions, for example, include aqueous or non-aqueous solutions or suspensions (such as emulsifiable concentrates, emulsions, flowables, dispersions, or solutions) or aerosols. Liquid compositions also include, in particular, emulsifiable concentrates, dispersions, emulsions, flowables, aerosols, wettable powders (or powder for spraying), dry flowables or pastes as forms of compositions which are liquid or intended to form liquid compositions when applied, for example as aqueous sprays (including low and ultra-low volume) or as fogs or aerosols.

Liquid compositions, for example, in the form of emulsifiable or soluble concentrates most frequently comprise about 5 to about 80% by weight of the active ingredient, while the emulsions or solutions which are ready for application contain, in their case, about 0.01 to about 20% of the active ingredient. Besides the solvent, the emulsifiable or soluble concentrates may contain, when required, about 2 to about 50% of suitable additives, such as stabilizers, surface-active agents, penetrating agents, corrosion inhibitors, colorants or adhesives. Emulsions of any required concentration, which are particularly suitable for application, for example, to plants, may be obtained from these concentrates by dilution with water. These compositions are included within the scope of the compositions which may be employed in the present invention. The emulsions may be in the form of water-in-oil or oil-in-water type and they may have a thick consistency.

The liquid compositions of this invention may, in addition to normal agricultural use applications be used for example to treat substrates or sites infested or liable to infestation by arthropods (or other pests controlled by compounds of this invention) including premises, outdoor or indoor storage or processing areas, containers or equipment or standing or running water.

All these aqueous dispersions or emulsions or spraying mixtures can be applied, for example, to crops by any suitable means, chiefly by spraying, at rates which are generally of the order of about 100 to about 1,200 liters of spraying mixture per hectare, but may be higher or lower (eg. low or ultra-low volume) depending upon the need or application technique. The compound or compositions according to the invention are conveniently applied to vegetation and in particular to roots or leaves having pests to be eliminated. Another method of application of the compounds or compositions according to the invention is by chemigation, that is to say, the addition of a formulation containing the active ingredient to irrigation water. This irrigation may be sprinkler irrigation for foliar pesticides or it can be ground irrigation or underground irrigation for soil or for systemic pesticides.

The concentrated suspensions, which can be applied by spraying, are prepared so as to produce a stable fluid product which does not settle (fine grinding) and usually contain from about 10 to about 75% by weight of active ingredient, from about 0.5 to about 30% of surface-active agents, from about 0.1 to about 10% of thixotropic agents, from about 0 to about 30% of suitable additives, such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrating agents, adhesives and, as the carrier, water or an organic liquid in which the active ingredient is poorly soluble or insoluble Some organic solids or inorganic salts may be dissolved in the carrier to help prevent settling or as antifreezes for water.

The wettable powers (or powder for spraying) are usually prepared so that they contain from about 10 to about 80% by weight of active ingredient, from about 20 to about 90% of a solid carrier, from about 0 to about 5% of a wetting agent, from about 3 to about 10% of a dispersing agent and, when necessary, from about 0 to about 80% of one or more stabilizers and/or other additives, such as penetrating agents, adhesives, anti-caking agents, colorants, or the like. To obtain these wettable powders, the active ingredient is thoroughly mixed in a suitable blender with additional substances which may be impregnated on the porous filler and is ground using a mill or other suitable grinder. This produces wettable powders, the wettability and the suspendability of which are advantageous. They may be suspended in water to give any desired concentration and this suspension can be employed very advantageously in particular for application to plant foliage.

The “water dispersible granules (WG)” (granules which are readily dispersible in water) have compositions which are substantially close to that of the wettable powders. They may be prepared by granulation of formulations described for the wettable powders, either by a wet route (contacting finely divided active ingredient with the inert filler and a little water, e.g. 1 to 20% by weight, or with an aqueous solution of a dispersing agent or binder, followed by drying and screening), or by a dry route (compacting followed by grinding and screening).

The rates and concentrations of the formulated compositions may vary according to the method of application or the nature of the compositions or use thereof. Generally speaking, the compositions for application to control arthropod or helminth pests usually contain from about 0.00001% to about 95%, more particularly from about 0.0005% to about 50% by weight of one or more compounds of the invention, or of total active ingredients (that is to say the compounds of the invention, together with other substances toxic to arthropods or helminths, synergists, trace elements or stabilizers). The actual compositions employed and their rate of application will be selected to achieve the desired effect(s) by the farmer, livestock producer, medical or veterinary practitioner, pest control operator or other person skilled in the art. Solid or liquid compositions for application topically to animals, timber, stored products or household goods usually contain from about 0.00005% to about 90%, more particularly from about 0.001% to about 10%, by weight of one or more compounds of the invention. For administration to animals orally or parenterally, including percutaneously solid or liquid compositions, these normally contain from about 0.1% to about 90% by weight of one or more compounds of the invention. Medicated feedstuffs normally contain from about 0.001% to about 3% by weight of one or more compounds of the invention. Concentrates or supplements for mixing with feedstuffs normally contain from about 5% to about 90%, preferably from about 5% to about 50%, by weight of one or more compounds of the invention. Mineral salt licks normally contain from about 0.1% to about 10% by weight of one or more compounds of formula (I) or pesticidally acceptable salts thereof.

Dusts or liquid compositions for application to livestock, goods, premises or outdoor areas may contain from about 0.0001% to about 15%, more especially from about 0.005% to about 2.0%, by weight, of one or more compounds of the invention. Suitable concentrations in treated waters are between about 0.0001 ppm and about 20 ppm, more particularly about 0.001 ppm to about 5.0 ppm. of one or more compounds of the invention, and may be used therapeutically in fish farming with appropriate exposure times. Edible baits may contain from about 0.01% to about 5%, preferably from about 0.01% to about 1.0%, by weight, of one or more compounds of the invention.

When administered to vertebrates parenterally, orally or by percutaneous or other means, the dosage of compounds of the invention, will depend upon the species, age, or health of the vertebrate and upon the nature and degree of its actual or potential infestation by arthropod or helminth pests. A single dose of about 0.1 to about 100 mg, preferably about 2.0 to about 20.0 mg, per kg body weight of the animal or doses of about 0.01 to about 20.0 mg, preferably about 0.1 to about 5.0 mg, per kg body weight of the animal per day, for sustained medication, are generally suitable by oral or parenteral administration. By use of sustained release formulations or devices, the daily doses required over a period of months may be combined and administered to animals on a single occasion.

The following composition EXAMPLES 2A-2M illustrate compositions for use against arthropods, especially insects or acarids, or helminths such as plant nematodes, which comprise, as active ingredient, compounds of the invention, such as those described in preparative examples. The compositions described in EXAMPLES 2A-2M can each be diluted to give a sprayable compositon at concentrations suitable for use in the field. Generic chemical descriptions of the ingredients (for which all of the following percentages are in weight percent), used in the composition EXAMPLES 2A-2M exemplified below, are as follows: Trade Name Chemical Description Ethylan BCP Nonylphenol ethylene oxide condensate Soprophor BSU Tristyrylphenol ethylene oxide condensate Arylan CA A 70% w/v solution of calcium dodecylbenzenesulfonate Solvesso 150 Light C₁₀ aromatic solvent Arylan S Sodium dodecylbenzenesulfonate Darvan NO₂ Sodium lignosulphonate Celite PF Synthetic magnesium silicate carrier Sopropon T36 Sodium salts of polycarboxylic acids Rhodigel 23 Polysaccharide xanthan gum Bentone 38 Organic derivative of magnesium montmorillonite Aerosil Microfine silicon dioxide

Example 2A

A water soluble concentrate is prepared with the composition as follows: Active ingredient 7% Ethylan BCP 10% N-methylpyrrolidone 83%

To a solution of Ethylan BCP dissolved in a portion of N-methylpyrrolidone is added the active ingredient with heating and stirring until dissolved. The resulting solution is made up to volume with the remainder of the solvent.

Example 2B

An emulsifiable concentrate (EC) is prepared with the composition as follows: Active ingredient 25% (max) Soprophor BSU 10% Arylan CA  5% N-methylpyrrolidone 50% Solvesso 150 10%

The first three components are dissolved in N-methylpyrrolidone and to this is then added the Solvesso 150 to give the final volume.

Example 2C

A wettable powder (WP) is prepared with the composition as follows: Active ingredient 40% Arylan S 2% Darvan NO₂ 5% Celite PF 53%

The ingredients are mixed and ground in a hammer-mill to a powder with a particle size of less than 50 microns.

Example 2D

An aqueous-flowable formulation is prepared with the composition as follows: Active ingredient 40.00% Ethylan BCP 1.00% Sopropon T360. 0.20% Ethylene glycol 5.00% Rhodigel 230. 0.15% Water 53.65%

The ingredients are intimately mixed and are ground in a bead mill until a mean particle size of less than 3 microns is obtained.

Example 2E

An emulsifiable suspension concentrate is prepared with the composition as follows: Active ingredient 30.0% Ethylan BCP 10.0% Bentone 38 0.5% Solvesso 150 59.5%

The ingredients are intimately mixed and ground in a beadmill until a mean particle size of less than 3 microns is obtained.

Example 2F

A water dispersible granule is prepared with the composition as follows: Active ingredient 30% Darvan No 2 15% Arylan S 8% Celite PF 47%

The ingredients are mixed, micronized in a fluid-energy mill and then granulated in a rotating pelletizer by spraying with water (up to 10%). The resulting granules are dried in a fluid-bed drier to remove excess water.

Example 2G

A dusting powder is prepared with the composition as follows: Active ingredient  1 to 10% Talc powder-superfine 99 to 90%

The ingredients are intimately mixed and further ground as necessary to achieve a fine powder. This powder may be applied to a locus of arthropod infestation, for example refuse dumps, stored products or household goods or animals infested by, or at risk of infestation by, arthropods to control the arthropods by oral ingestion. Suitable means for distributing the dusting powder to the locus of arthropod infestation include mechanical blowers, handshakers or livestock self treatment devices.

Example 2H

An edible bait is prepared with the composition as follows: Active ingredient 0.1 to 1.0% Wheat flour 80% Molasses 19.9 to 19%  

The ingredients are intimately mixed and formed as required into a bait form. This edible bait may be distributed at a locus, for example domestic or industrial premises, e.g. kitchens, hospitals or stores, or outdoor areas, infested by arthropods, for example ants, locusts, cockroaches or flies, to control the arthropods by oral ingestion.

Example 21

A solution formulation is prepared with a composition as follows: Active ingredient 15% Dimethyl sulfoxide 85%

The active ingredient is dissolved in dimethyl sulfoxide with mixing and or heating as required. This solution may be applied percutaneously as a pour-on application to domestic animals infested by arthropods or, after sterilization by filtration through a polytetrafluoroethylene membrane (0.22 micrometer pore size), by parenteral injection, at a rate of application of from 1.2 to 12 ml of solution per 100 kg of animal body weight.

Example 2J

A wettable powder is prepared with the composition as follows: Active ingredient 50% Ethylan BCP 5% Aerosil 5% Celite PF 40%

The Ethylan BCP is absorbed onto the Aerosil which is then mixed with the other ingredients and ground in a hammer-mill to give a wettable powder, which may be diluted with water to a concentration of from 0.001% to 2% by weight of the active compound and applied to a locus of infestation by arthropods, for example, dipterous larvae or plant nematodes, by spraying, or to domestic animals infested by, or at risk of infection by arthropods, by spraying or dipping, or by oral administration in drinking water, to control the arthropods.

Example 2K

A slow release bolus composition is formed from granules containing the following components in varying percentages (similar to those described for the previous compositions) depending upon need: Active ingredient Density agent Slow-release agent Binder

The intimately mixed ingredients are formed into granules which are compressed into a bolus with a specific gravity of 2 or more. This can be administered orally to ruminant domestic animals for retention within the reticulo-rumen to give a continual slow release of active compound over an extended period of time to control infestation of the ruminant domestic animals by arthropods.

Example 2L

A slow release composition in the form of granules, pellets, brickettes or the like can be prepared with compositions as follows: Active ingredient 0.5 to 25% Polyvinyl chloride  75 to 99.5% Dioctyl phthalate (plasticizer)

The components are blended and then formed into suitable shapes by melt-extrusion or molding. These composition are useful, for example, for addition to standing water or for fabrication into collars or eartags for attachment to domestic animals to control pests by slow release.

Example 2M

A water dispersible granule is prepared with the composition as follows: Active ingredient 85%(max) Polyvinylpyrrolidone  5% Attapulgite clay  6% Sodium lauryl sulfate  2% Glycerine  2%

The ingredients are mixed as a 45% slurry with water and wet milled to a particle size of 4 microns, then spray-dried to remove water.

Methods of Pesticidal use

The following representative test procedures, using compounds of the invention, were conducted to determine the parasiticidal and pesticidal activity of compounds of the invention.

Method A:

Germinated field bean seeds (Vicia faba) with seed roots were transferred into brown glass bottles filled with tap water and then populated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then dipped into an aqueous solution of the formulated preparation to be examined for 5 seconds. After they had drained, plants and animals were stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days of storage, the effect of the preparation on the aphids was determined. At a concentration of 100 ppm (based on the content of active compound), the following Compounds caused a mortality of at least 50% among the aphids:

A-18, A-64, A-65, A-71, A-74, A-79, A-81, A-86, A-88, A-206, A-209, A-223, A-255, A-261, A-262, A-265, A-267, A-268, A-292, A-296, A-312, A-312, A-316, A-317, A-326, A-329, A-349, A-353, A-354, A-355, A-365, A-366, A-367, A-369, A-373, A-381, A-398, A-431, A-524, A-529, A-540, A-544, A-564, A-605, A-626, A-691, A-697, A-713, A-736, A-737, A-738, A-744, A-745, A-747, A-748, A-798, A-799, A-805, A-822, A-861, A-862, A-865, A-867, A-874, B-37, B-40, B-47, B-65, B-74, B-149, B-150, B-151, B-152, B-155, B-158, B-163, B-166, B-167, B-168, B-169, B-170, B-176, B-184, B-185, B-189, B-247, B-251, B-255, B-258, B-259, B-261, B-267, B-269, B-296, B-313, B-349, B-353, B-354, B-355, B-366, B-369, B-373, B-398, B-431, B-564, B-713, B-736, B-737, B-738, B-744, B-745, B-747, B748, B-799, B-805, B-822, B-861, B-863, B-864, B-865, B-867, B-869, B-870, B-871, B-873, B-874, B-877, C-85, E-85, F-85, F-88, H-85, S-548, S-550, S-551, S-552, S-553, S-555, S-556, S-558, S-559, U-3, U-7, U-20, X-45 and X-55.

Method B:

Germinated field bean seeds (Vicia faba) with seed roots were transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined were pipetted into the brown glass bottle. The field bean was then heavily populated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days of storage, the root-systemic effect of the preparation on the aphids was determined. At a concentration of 10 ppm (based on the content of active compound), the following Compounds caused a mortality of at least 80% among the aphids, by root-systemic action:

A-39, A-64, A-65, A-67, A-71, A-74, A-79, A-81, A-86, A-88, A-89, A-90, A-209, A-212, A-223, A-262, A-265, A-267, A-268, A-292, A-296, A-313, A-317, A-326, A-329, A-349, A-354, A-355, A-365, A-366, A-367, A-369, A-373, A-381, A-398, A-431, A-519, A-524, A-529, A-540, A-544, A-564, A-605, A-626, A-691, A-697, A-713, A-736, A-737, A-738, A-744, A-745, A-747, A-748, A-798, A-799, A-805, A-822, A-861, A-862, A-865, A-867, A-871, A-873, A-874, B-37, B-40, B-47, B-65, B-71, B-74, B-86, B-149, B-150, B-151, B-152, B-155, B-158, B-166, B-167, B-169, B-170, B-176, B-184, B-189, B-247, B-251, B-255, B-257, B-258, B-259, B-261, B-267, B-269, B-296, B-313, B-349, B-353, B-354, B-355, B-366, B-369, B-373, B-398, B-564, B-713, B-736, B-737, B-738, B-744, B-745, B-748, B-799, B-805, B-861, B-863, B-864, B-865, B-867, B-869, B-870, B-871, B-872, B-873, B-874, B-877, C-85, D-86, E-85, F-85, F-88, G-85, H-85, S-3, S-120, S-356, S-548, S-550, S-551, S-553, S-556, S-557, S-558, S-559, U-3, U-7, U-20, X-45 and X-55. 

1. A compound of the formula (I):

wherein: R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a); R² is H, (C₁-C₆)alkyl or R³; R³ is R⁵, OH or NH₂; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);

R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more (C₁-C₆)alkyl, (C₁-C₆)haloalkyl or R⁶ groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups are substituted by one or more R⁶ groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or substituted by one or more R⁶ groups; R⁴ is H or R⁵; or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups; R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, CO(C₁-C₆)alkyl, NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl or SO₂(C₁-C₆)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is NH(CHR¹⁴)_(s)aryl, —(CR¹⁵R¹⁶)_(p)aryl, O(R¹⁵R¹⁶)_(r)aryl, NHCOaryl, CO(CH₂)_(t)aryl, NHSO₂aryl, SO₂(CH₂)_(u)aryl or N═C(aryl)₂, —(CR¹⁵R¹⁶)_(p)heterocyclyl or O(R¹⁵R¹⁶)_(r)heterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; or is O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl or N═C[(C₁-C₆)alkyl]₂; R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(4a), CN, CO₂(C₁-C₆)alkyl, CO₂H, NO₂, OH, amino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, carbamoyl, (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl or CH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by one or more R^(14a) or halogen groups; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S, O or NR¹⁸; V is O or S; W is (CHR¹⁹)_(q), CO or NR²⁰; X is CR²¹ or N; Y is CR²² or N; Z is O, CO or NR²³; R⁷, R⁸, R⁹, R¹², R¹⁹, R²¹ and R²² are each independently H; or (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy or (C₂-C₆)alkynyloxy, which last seven mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl, which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom may represent C═O; R¹⁰, R²⁰ and R²³ are each independently H; or (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or (C₃-C₈)cycloalkyl, which last four mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; R¹¹ is R⁷, halogen, CN, CO₂(C₁-C₆)alkyl, NO₂ or S(O)_(n)R¹⁴; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; R¹³ is R⁷ or OH; R¹⁴, R¹⁵ and R¹⁶ are each independently H, (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R¹⁸ is R⁷ or OH; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; m is zero or one; n, p, r, s, t and u are each independently zero, one or two; q is one, two or three; and each heterocyclyl in the above mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1 to 4 hetero atoms selected from N, O and S; or a pesticidally acceptable salt thereof; with the exclusion of the compound wherein R¹ is —C(═U)NR³R⁴; U is O; R² is H; m is zero; R⁴ is H and R³ is 2,4-dichlorophenyl.
 2. A compound according to claim 1 wherein: R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a); R² is H, (C₁-C₆)alkyl or R³; R³ is R⁵, OH or NH₂; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);

R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups are substituted by one or more R⁶ groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or substituted by one or more R⁶ groups; R⁴ is H or R⁵; or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups; R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, CO(C₁-C₆)alkyl, NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl or SO₂(C₁-C₆)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is NH(CHR¹⁴)_(s)aryl, —(CR¹⁵R¹⁶)_(p)aryl, O(R¹⁵R¹⁶)_(r)aryl, NHCOaryl, CO(CH₂)_(t)aryl, NHSO₂aryl, SO₂(CH₂)_(u)aryl or N═C(aryl)₂, —(CR¹⁵R¹⁶)_(p)heterocyclyl or O(R¹⁵R¹⁶)_(r)heterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; or is O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl or N═C[(C₁-C₆)alkyl]₂; R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(4a), CN, CO₂(C₁-C₆)alkyl, CO₂H, NO₂, OH, amino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, carbamoyl, (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl or CH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by one or more R^(14a) or halogen groups; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S, O or NR¹⁸; V is O or S; W is (CHR¹⁹)_(q), CO or NR²⁰; X is CR²¹ or N; Y is CR²² or N; Z is O, CO or NR²³; R⁷, R⁸, R⁹, R¹², R¹⁹, R²¹ and R²² are each independently H; or (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy or (C₂-C₆)alkynyloxy, which last seven mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl, which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom may represent C═O; R¹⁰, R²⁰ and R²³ are each independently H; or (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or (C₃-C₈)cycloalkyl, which last four mentioned groups are unsubstituted or substituted by one or more R⁶ groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R⁶ groups; R¹¹ is R⁷, halogen, CN, CO₂(C₁-C₆)alkyl, NO₂ or S(O)_(n)R¹⁴; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; R¹³ is R⁷ or OH; R¹⁴, R¹⁵ and R¹⁶ are each independently H, (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; R¹⁸ is R⁷ or OH; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are unsubstituted or substituted by one or more R⁶ groups; m is zero or one; n, p, r, s, t and u are each independently zero, one or two; q is one, two or three; and each heterocyclyl in the above mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1 to 4 hetero atoms selected from N, O and S; or a pesticidally acceptable salt thereof; with the exclusion of the compound wherein R¹ is —C(═U)NR³R⁴; U is O; R² is H; m is zero; R⁴ is H and R³ is 2,4-dichlorophenyl.
 3. A compound or a salt thereof as claimed in claim 1, wherein R¹ is —C(═U)NR³R⁴.
 4. A compound or a salt thereof as claimed in claim 1, wherein R² is H or R³.
 5. A compound or a salt thereof as claimed in claim 1, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


6. A compound or a salt thereof as claimed in claim 1, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 7. A compound or a salt thereof as claimed in claim 1, wherein R¹ is —C(═U)NR³R⁴; R² is H; R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms may form a heterocyclic ring selected from (A) and (C):

R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl or thiomorpholin-1-yl (or its S-oxide or S,S-dioxide) ring; R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl, O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R¹⁷ groups; R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, NO₂ or OH; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S or O; W is (CHR¹⁹)_(q) or CO; Z is O; R⁷, R⁸, R⁹, R¹⁰ and R¹⁹ are each H; or (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R⁷ and R⁸ together with the attached carbon atom represent C═O; R¹⁴, R¹⁵ and R¹⁶ are each H or (C₁-C₆)alkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; m is zero; n, r, s, t and u are zero, one or two; q is one; and wherein heterocyclyl denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,2,4)-thiadiazole, (1,3,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane radical.
 8. A compound or a salt thereof as claimed in claim 1, wherein R¹ is —C(═U)NR³R⁴; R² is H; U is O or S; R³ is (C₁-C₆)alkoxy, C₁-C₆)haloalkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, CH₂phenyl or OCH₂phenyl, phenyl or 2-pyridyl which last four mentioned phenyl or pyridyl groups are unsubstituted or substituted by one or more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN and NO₂; R⁴ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl; and m is zero.
 9. A process for the preparation of a compound of formula (I) or a salt thereof as defined in claim 1, which process comprises: a) where R¹ is —C(═U)NR³R⁴, m is zero, and R², U, R³ and R⁴ are as defined in formula (I); or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹², R¹², R¹³, W, X, Y and Z are as defined in formula (I), reacting a compound of formula (II):

wherein L is a leaving group, with a compound of formula (III): HNR²—C(═U)NR³R⁴  (III) wherein R², U, R³ and R⁴ are as defined in formula (I), or with a compound of formula (IV), (V), (VI); (VII) or (VIII):

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, W, X, Y and Z are as defined in formula (I); or b) where R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O, and R³ and R⁴ are as defined in formula (I), reacting a compound of formula (IX):

with oxalyl chloride or triphosgene, to give the corresponding acylisocyanate intermediate followed by reacting the resultant intermediate with an amine of formula (X): HNR³R⁴  (X) wherein R³ and R⁴ are as defined in formula (I); or c) where R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O, and R^(3a) is as defined in formula (I), reacting a compound of formula (IX) above, with oxalyl chloride to give an acylisocyanate intermediate, followed by reacting the resultant intermediate with an alcohol of formula (XI): HOR^(3a)  (XI) wherein R³ is as defined in formula (I); or d) where R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O or S, and R³ and R⁴ are as defined in formula (I), reacting a compound of formula (XII):

wherein U is O or S, with a compound of formula (X) as defined in formula (I); or e) where R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O or S, and R^(3a) is as defined in formula (I), reacting a compound of formula (XIII):

wherein V is O or S, with a compound of formula (XI) as defined above; or f) where R¹ is —C(═U)NR³R⁴, m is zero, R² is H, R⁴ is H, U is O or S, and R³ is as defined in formula (I), reacting a compound of formula (IX) as defined in formula (I), with a strong base, followed reacting with a compound of formula (XIV): R³N═C═U  (XIV) wherein R³ is as defined in formula (I); or g) where R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a), m is zero, R² is H, U and V are each S, and R³, R^(3a) and R⁴ are as defined in formula (I), as a 1-pot reaction, reacting 4-trifluoromethylnicotinic acid with a halogenating agent to give the corresponding acid chloride, followed by reacting the acid chloride with an alkali metal thiocyanate or ammonium thiocyanate or a tetraalkylammonium thiocyanate to give the 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, followed by reacting the isothiocyanate with an amine of formula (X) above or an alcohol of formula (XI) above; or h) where R¹ and R² are as defined above, and m is 1 oxidizing a corresponding compound in which m is 0; and if desired, converting a resulting compound of formula (I) into a pesticidally acceptable salt thereof.
 10. A pesticidal composition comprising a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in claim 1, in association with a pesticidally acceptable diluent or carrier and/or surface active agent.
 11. (canceled)
 12. A compound or salt thereof as claimed in claim 2, wherein R¹ is —C(═U)NR³, R⁴.
 13. A compound or salt thereof as claimed in claim 2, wherein R² is H or R³.
 14. A compound or salt thereof as claimed in claim 3, wherein R² is H or R³.
 15. A compound or salt thereof as claimed in claim 12, wherein R² is H or R³.
 16. A compound or salt thereof as claimed in claim 2, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


17. A compound or salt thereof as claimed in claim 3, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


18. A compound or salt thereof as claimed in claim 4, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


19. A compound or salt thereof as claimed in claim 12, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


20. A compound or salt thereof as claimed in claim 13, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


21. A compound or salt thereof as claimed in claim 14, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


22. A compound or salt thereof as claimed in claim 15, wherein R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; or R² and R³ together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):


23. A compound or salt thereof as claimed in claim 2, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 24. A compound or salt thereof as claimed in claim 3, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 25. A compound or salt thereof as claimed in claim 4, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 26. A compound or salt thereof as claimed in claim 5, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 27. A compound or salt thereof as claimed in claim 12, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 28. A compound or salt thereof as claimed in claim 13, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 29. A compound or salt thereof as claimed in claim 14, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 30. A compound or salt thereof as claimed in claim 15, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 31. A compound or salt thereof as claimed in claim 16, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 32. A compound or salt thereof as claimed in claim 17, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 33. A compound or salt thereof as claimed in claim 18, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 34. A compound or salt thereof as claimed in claim 19, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 35. A compound or salt thereof as claimed in claim 20, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 36. A compound or salt thereof as claimed in claim 21, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 37. A compound or salt thereof as claimed in claim 22, wherein R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups; or R³ and R⁴ together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R⁶ or R^(14a) groups.
 38. A method for the control of arthropod or nematode pests, said method comprising applying to said pests or to a locus at which they reside or feed or which is susceptible to infestation thereby, a pesticidally effective amount of a compound or salt thereof as claimed in claim
 1. 39. A method for the control of arthropod or nematode pests, said method comprising applying to said pests or to a locus at which they reside or feed or which is susceptible to infestation thereby, a pesticidally effective amount of a composition as claimed in claim
 10. 